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109-12-6 Usage

Chemical Properties

white to light yellow powder

Uses

2-Aminopyrimidine is used in the synthesis of sulfonamides as isoform-selective inhibitors with efficacy in rodent pain models.

Definition

ChEBI: An aminopyrimidine carrying an amino group at position 2.

Synthesis Reference(s)

Tetrahedron Letters, 39, p. 1313, 1998 DOI: 10.1016/S0040-4039(97)10877-2

Purification Methods

Crystallise 2-aminopyrimidine from *C6H6, EtOH or H2O. [Beilstein 25 III/IV 2071.]

Check Digit Verification of cas no

The CAS Registry Mumber 109-12-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 109-12:
(5*1)+(4*0)+(3*9)+(2*1)+(1*2)=36
36 % 10 = 6
So 109-12-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H5N3/c5-4-6-2-1-3-7-4/h1-3H,(H2,5,6,7)

109-12-6 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • TCI America

  • (A0412)  2-Aminopyrimidine  >98.0%(GC)(T)

  • 109-12-6

  • 25g

  • 240.00CNY

  • Detail
  • Alfa Aesar

  • (B24594)  2-Aminopyrimidine, 98%   

  • 109-12-6

  • 100g

  • 269.0CNY

  • Detail
  • Alfa Aesar

  • (B24594)  2-Aminopyrimidine, 98%   

  • 109-12-6

  • 500g

  • 1099.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001469)  SulfadiazineimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 109-12-6

  • Y0001469

  • 1,880.19CNY

  • Detail
  • Aldrich

  • (A78608)  2-Aminopyrimidine  97%

  • 109-12-6

  • A78608-100G

  • 253.89CNY

  • Detail
  • Aldrich

  • (A78608)  2-Aminopyrimidine  97%

  • 109-12-6

  • A78608-500G

  • 1,422.72CNY

  • Detail
  • Vetec

  • (V900286)  2-Aminopyrimidine  Vetec reagent grade, 97%

  • 109-12-6

  • V900286-100G

  • 256.23CNY

  • Detail

109-12-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name pyrimidin-2-amine

1.2 Other means of identification

Product number -
Other names 2-pyrimidineamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-12-6 SDS

109-12-6Synthetic route

Malondialdehyde
542-78-9

Malondialdehyde

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
97%
2-bromopyrimidine
4595-60-2

2-bromopyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;94%
nitro-pyrimidine
79917-54-7

nitro-pyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With triethylamine In water at 80℃; for 8h; Inert atmosphere; Green chemistry; chemoselective reaction;90%
With sodium tetrahydroborate In methanol; water at 40℃; for 0.5h; Green chemistry;
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

O-potassio-2,4-dimethyl-3-pentanone
51689-86-2

O-potassio-2,4-dimethyl-3-pentanone

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

2,4-Dimethyl-2-pyrimidin-2-yl-pentan-3-one
75782-24-0

2,4-Dimethyl-2-pyrimidin-2-yl-pentan-3-one

C

2-(2-chloropyrimidin-4-yl)-2,4-dimethyl-3-pentanone
75782-25-1

2-(2-chloropyrimidin-4-yl)-2,4-dimethyl-3-pentanone

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.25h; Product distribution; Mechanism; Irradiation; effect of inhibitor (di-tert-butyl-nitroxide) and exclusion of light;A 4%
B 88%
C n/a
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With potassium amide In diethyl ether; ammonia for 0.25h; exclusion of light;88%
With ammonia at 20℃; Kinetics;
With ammonia at 80℃; under 67506.8 Torr; Kinetics; Temperature;
2-amino-pyrimidine-5-carboxylic acid
3167-50-8

2-amino-pyrimidine-5-carboxylic acid

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
for 3h; Heating;74%
tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

benzene
71-43-2

benzene

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

phenyl-pyrimidin-2-yl-amine
57356-49-7

phenyl-pyrimidin-2-yl-amine

C

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 8h; Irradiation;A 11%
B 66%
C n/a
With trifluoroacetic acid at 25℃; for 8h; Product distribution; with/without heavy-atom solvent (CH2CCl2, CH2Br2); other solvent; other reag; other temp.;A 11%
B 66%
C n/a
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

potassium enolate of acetone
128190-66-9, 25088-58-8

potassium enolate of acetone

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

1-(2-pyrimidinyl)-2-propanone
75782-22-8

1-(2-pyrimidinyl)-2-propanone

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.25h; Mechanism; Product distribution; Irradiation; effect of inhibitor (di-tert-butyl-nitroxide) and exclusion of light;A 4%
B 61%
pyrimidin-2-yl-carbamic acid benzyl ester
191487-39-5

pyrimidin-2-yl-carbamic acid benzyl ester

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

isocytosine
108-53-2

isocytosine

C

(6-Oxo-1,6-dihydro-pyrimidin-2-yl)-carbamic acid benzyl ester

(6-Oxo-1,6-dihydro-pyrimidin-2-yl)-carbamic acid benzyl ester

Conditions
ConditionsYield
With Rhodococcus erythropolis DSM 6138 In ethanol for 16h;A n/a
B n/a
C 58%
2-(N-sulphinylamino)pyrimidine
110526-12-0

2-(N-sulphinylamino)pyrimidine

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

(endo)-3-(2-pyrimidinyl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2-oxide

(endo)-3-(2-pyrimidinyl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2-oxide

exo-3-(2-pyrimidinyl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2-oxide

exo-3-(2-pyrimidinyl)-2λ4-thia-3-azabicyclo[2.2.2]oct-5-ene 2-oxide

Conditions
ConditionsYield
In tetrahydrofuran at -75℃; for 22h; hetero-Diels-Alder reaction;A n/a
B 14%
C 51%
para-xylene
106-42-3

para-xylene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

1,4-dimethyl-2-(4-methylbenzyl)benzene
721-45-9

1,4-dimethyl-2-(4-methylbenzyl)benzene

C

2-(2,5-dimethylanilino)pyrimidine

2-(2,5-dimethylanilino)pyrimidine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 8h; Irradiation;A 27%
B 9.8%
C 47%
methoxybenzene
100-66-3

methoxybenzene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

(4-methoxy-phenyl)-pyrimidin-2-yl-amine
137379-63-6

(4-methoxy-phenyl)-pyrimidin-2-yl-amine

C

(2-methoxy-phenyl)-pyrimidin-2-yl-amine

(2-methoxy-phenyl)-pyrimidin-2-yl-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 6h; Product distribution; other reag; other reaction time;A 5%
B 33%
C 40%
With trifluoroacetic acid at 25℃; for 8h; Irradiation;A 20%
B 24%
C 28%
tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

toluene
108-88-3

toluene

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

Diphenylmethane
101-81-5

Diphenylmethane

C

N-(4-tolyl)pyrimidin-2-amine
198711-26-1

N-(4-tolyl)pyrimidin-2-amine

D

2-methyl-N-(2-pyrimidyl)aniline

2-methyl-N-(2-pyrimidyl)aniline

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 8h; Irradiation; Title compound not separated from byproducts;A 18 % Chromat.
B 11 % Chromat.
C 19 % Chromat.
D 39%
tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

toluene
108-88-3

toluene

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

Diphenylmethane
101-81-5

Diphenylmethane

C

N-(4-tolyl)pyrimidin-2-amine
198711-26-1

N-(4-tolyl)pyrimidin-2-amine

D

2-methyl-N-(2-pyrimidyl)aniline

2-methyl-N-(2-pyrimidyl)aniline

E

N-(3-methylphenyl)pyrimidin-2-amine

N-(3-methylphenyl)pyrimidin-2-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 6h; Product distribution; other reag; other reaction time;A 13%
B 5%
C 23%
D 38%
E 2.2%
ethylbenzene
100-41-4

ethylbenzene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

1-ethyl-4-(1-phenylethyl)benzene
6196-94-7, 71886-67-4

1-ethyl-4-(1-phenylethyl)benzene

C

1-(o-ethylphenyl)-1-phenylethane
18908-70-8

1-(o-ethylphenyl)-1-phenylethane

D

N-(4-ethylphenyl)pyrimidin-2-amine

N-(4-ethylphenyl)pyrimidin-2-amine

E

(3-Ethyl-phenyl)-pyrimidin-2-yl-amine

(3-Ethyl-phenyl)-pyrimidin-2-yl-amine

F

N-(2-ethylphenyl)pyrimidin-2-amine

N-(2-ethylphenyl)pyrimidin-2-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 6h; Product distribution; other reag; other reaction time;A 1%
B n/a
C n/a
D 32%
E 0.8%
F 36%
2‐aminopyrimidine‐1‐oxide
35034-15-2

2‐aminopyrimidine‐1‐oxide

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

5-chloropyrimidin-2-amine
5428-89-7

5-chloropyrimidin-2-amine

C

5-chloro-2-aminopyrimidine 1-oxide

5-chloro-2-aminopyrimidine 1-oxide

Conditions
ConditionsYield
With hydrogenchloride; sodium nitriteA 34%
B 8.5%
C 6%
chlorobenzene
108-90-7

chlorobenzene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

(4-chloro-phenyl)-pyrimidin-2-yl-amine

(4-chloro-phenyl)-pyrimidin-2-yl-amine

C

(3-chloro-phenyl)-pyrimidin-2-yl-amine
214627-66-4

(3-chloro-phenyl)-pyrimidin-2-yl-amine

D

(2-chloro-phenyl)-pyrimidin-2-yl-amine

(2-chloro-phenyl)-pyrimidin-2-yl-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 8h; Irradiation;A 34%
B 6.2%
C 0.4%
D 21%
para-xylene
106-42-3

para-xylene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

biphenyl
92-52-4

biphenyl

C

2-(2,5-dimethylanilino)pyrimidine

2-(2,5-dimethylanilino)pyrimidine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 6h; Product distribution; with/without heavy-atom solvent (CH2CCl2, CH2Br2); other solvent; other reag; other reaction time;A 19%
B n/a
C 34%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

O-potassio-3,3-dimethyl-2-butanone
351531-29-8

O-potassio-3,3-dimethyl-2-butanone

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

1-(2-pyrimidinyl)-3,3-dimethyl-2-butanone
75782-23-9

1-(2-pyrimidinyl)-3,3-dimethyl-2-butanone

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.25h; Mechanism; Product distribution; Irradiation;A 4%
B 32%
ethylbenzene
100-41-4

ethylbenzene

tetrazolo[1,5-a]pyrimidine
275-03-6

tetrazolo[1,5-a]pyrimidine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

N-(4-ethylphenyl)pyrimidin-2-amine

N-(4-ethylphenyl)pyrimidin-2-amine

C

(3-Ethyl-phenyl)-pyrimidin-2-yl-amine

(3-Ethyl-phenyl)-pyrimidin-2-yl-amine

D

N-(2-ethylphenyl)pyrimidin-2-amine

N-(2-ethylphenyl)pyrimidin-2-amine

Conditions
ConditionsYield
With trifluoroacetic acid at 25℃; for 8h; Irradiation; Further byproducts given. Title compound not separated from byproducts;A 27 % Chromat.
B 14 % Chromat.
C 4.8 % Chromat.
D 21%
N-benzylidene-N'-pyrimidin-2-ylhydrazine
65267-35-8

N-benzylidene-N'-pyrimidin-2-ylhydrazine

A

2-aminopyrimidine
109-12-6

2-aminopyrimidine

B

2,3-diphenyl quinoline
22514-82-5

2,3-diphenyl quinoline

C

lophine
484-47-9

lophine

D

benzonitrile
100-47-0

benzonitrile

E

2-phenyl<1,2,4>triazolo<1,5-a>pyrimidine
55643-77-1

2-phenyl<1,2,4>triazolo<1,5-a>pyrimidine

F

3-phenyl-[1,2,4]triazolo[4,3-a]pyrimidine
65267-36-9

3-phenyl-[1,2,4]triazolo[4,3-a]pyrimidine

Conditions
ConditionsYield
at 350℃; under 0.02 Torr; for 1h; Mechanism; Pyrolysis;A 18%
B 10%
C 16%
D 15%
E 17%
F 15%
1,3,3-triethoxypropene
5444-80-4

1,3,3-triethoxypropene

guanidine hydrochloride
50-01-1

guanidine hydrochloride

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With hydrogenchloride; ethanol
2-Amino-4,6-dichloropyrimidine
56-05-3

2-Amino-4,6-dichloropyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With water; zinc
With potassium hydroxide; palladium on activated charcoal Hydrogenation;
With sodium hydroxide; palladium on activated charcoal; diethyl ether Hydrogenation;
Propiolaldehyde diethyl acetal
10160-87-9

Propiolaldehyde diethyl acetal

guanidine nitrate
506-93-4

guanidine nitrate

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With hydrogenchloride
2-amino-4-chloropyrimidine
3993-78-0

2-amino-4-chloropyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With methanol; Lindlar's catalyst; barium(II) oxide Hydrogenation;
With Lindlar's catalyst; ethanol; barium(II) oxide Hydrogenation;
elektrochemischen Reduktion an einer Cadmium-Kathode;
diguanidine carbonate
593-85-1

diguanidine carbonate

propargyl alcohol
107-19-7

propargyl alcohol

2-aminopyrimidine
109-12-6

2-aminopyrimidine

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid
With chromium(VI) oxide; sulfuric acid
Propargylic aldehyde
624-67-9

Propargylic aldehyde

guanidine nitrate
113-00-8

guanidine nitrate

2-aminopyrimidine
109-12-6

2-aminopyrimidine

1,1-dichloro-3,3-dimethoxy-propane
89212-11-3

1,1-dichloro-3,3-dimethoxy-propane

guanidine nitrate
113-00-8

guanidine nitrate

2-aminopyrimidine
109-12-6

2-aminopyrimidine

3-butyryloxy-acrylaldehyde
98272-44-7

3-butyryloxy-acrylaldehyde

guanidine nitrate
113-00-8

guanidine nitrate

2-aminopyrimidine
109-12-6

2-aminopyrimidine

acetic acid-(1-bromo-3,3-dichloro-propyl ester)
98021-69-3

acetic acid-(1-bromo-3,3-dichloro-propyl ester)

guanidine nitrate
113-00-8

guanidine nitrate

2-aminopyrimidine
109-12-6

2-aminopyrimidine

2-aminopyrimidine
109-12-6

2-aminopyrimidine

5-bromo-2-aminopyrimidine
7752-82-1

5-bromo-2-aminopyrimidine

Conditions
ConditionsYield
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.0833333h;100%
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.5h;98%
With N-Bromosuccinimide In acetonitrile at 20℃; Cooling with ice; Darkness;97%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

2-chloroethanal
107-20-0

2-chloroethanal

imidazo[1,2-a]pyrimidine
274-95-3

imidazo[1,2-a]pyrimidine

Conditions
ConditionsYield
In ethanol Reflux;100%
With sodium hydrogencarbonate for 16h; Ambient temperature;75%
With sodium hydrogencarbonate In ethanol; water for 48h; Heating;
With sodium hydrogencarbonate In ethanol; water for 48h; Heating;
2-aminopyrimidine
109-12-6

2-aminopyrimidine

bromomethyl 2-methoxyphenyl ketone
31949-21-0

bromomethyl 2-methoxyphenyl ketone

2-(2-methoxyphenyl)imidazo[1,2-a]pyrimidine
143696-71-3

2-(2-methoxyphenyl)imidazo[1,2-a]pyrimidine

Conditions
ConditionsYield
In ethanol at 75℃; for 24h;100%
In ethanol Reflux;92%
In 1,2-dimethoxyethane for 48h; Heating;
With sodium hydrogencarbonate In 2-methyltetrahydrofuran at 85℃; for 10h; Sealed tube;
2-aminopyrimidine
109-12-6

2-aminopyrimidine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N,N-dimethyl-N'-pyrimidin-2-ylformamidine
6578-34-3

N,N-dimethyl-N'-pyrimidin-2-ylformamidine

Conditions
ConditionsYield
In toluene Heating;100%
for 6h; Reflux;80%
In toluene for 2h; Heating;
2-aminopyrimidine
109-12-6

2-aminopyrimidine

1,1-dichloro-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene
161868-74-2

1,1-dichloro-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene

1,1-di-<(pyrimidin-2-yl)amino>-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene

1,1-di-<(pyrimidin-2-yl)amino>-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;100%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

1-bromo-2-[4-(N-piperidinosulfonyl)phenyl]ethanedione 1-phenylhydrazone

1-bromo-2-[4-(N-piperidinosulfonyl)phenyl]ethanedione 1-phenylhydrazone

2-[4-(N-piperidinosulfonyl)phenyl]-3-phenylazoimidazo[1,2-a]pyrimidine

2-[4-(N-piperidinosulfonyl)phenyl]-3-phenylazoimidazo[1,2-a]pyrimidine

Conditions
ConditionsYield
With triethylamine In ethanol for 2h; Cyclization; Heating;100%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

1,1,1-Trifluoro-2,4-pentanedione
367-57-7

1,1,1-Trifluoro-2,4-pentanedione

4-methyl-2-trifluoromethyl-pyrimido-[1,2a]pyrimidine hydrogen sulfate

4-methyl-2-trifluoromethyl-pyrimido-[1,2a]pyrimidine hydrogen sulfate

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine; 1,1,1-Trifluoro-2,4-pentanedione
Stage #2: With sulfuric acid
100%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

2-amino-1H-imidazole-4-carboxylic acid ethyl ester
149520-94-5

2-amino-1H-imidazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine; ethyl Bromopyruvate In ethanol at 75℃; for 16h; Inert atmosphere;
Stage #2: With hydrazine hydrate In ethanol at 75℃; for 16h; Inert atmosphere;
100%
Stage #1: 2-aminopyrimidine; ethyl Bromopyruvate In ethanol at 75℃;
Stage #2: With hydrazine hydrate In ethanol at 75℃;
54%
Stage #1: 2-aminopyrimidine; ethyl Bromopyruvate In ethanol at 75℃; for 18h;
Stage #2: With hydrazine hydrate In ethanol at 75℃; for 16.5h;
0.34 g
2-aminopyrimidine
109-12-6

2-aminopyrimidine

1,4,5,6-tetrahydro-pyrimidin-2-ylamine
41078-65-3

1,4,5,6-tetrahydro-pyrimidin-2-ylamine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid at 20℃; under 760.051 Torr; for 17h; Time;100%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

benzyl alcohol
100-51-6

benzyl alcohol

2-(benzylamino)pyrimidine
4214-59-9

2-(benzylamino)pyrimidine

Conditions
ConditionsYield
With iron(II,III) oxide; potassium tert-butylate In 1,4-dioxane at 90℃; for 168h; Inert atmosphere;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 48h; Inert atmosphere;99%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

6-chloroquinoline
612-57-7

6-chloroquinoline

N-(pyrimidin-2-yl)quinolin-6-amine
1160861-67-5

N-(pyrimidin-2-yl)quinolin-6-amine

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate; ruphos In tert-butyl alcohol at 110℃; for 24h; Inert atmosphere;99%
With water; potassium carbonate; palladium diacetate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In tert-butyl alcohol at 110℃; for 1h; Inert atmosphere;91%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; C47H63NO2PPd(2+)*CH3O3S(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 24h;90%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

formaldehyd
50-00-0

formaldehyd

Glyoxal
131543-46-9

Glyoxal

2-(1H-imidazol-1-yl)pyrimidine
134914-65-1

2-(1H-imidazol-1-yl)pyrimidine

Conditions
ConditionsYield
With phosphoric acid; ammonium chloride In methanol Reflux;99%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

3-(chlorosulfonyl)benzenesulfonyl fluoride
2489-52-3

3-(chlorosulfonyl)benzenesulfonyl fluoride

3-(N-(pyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

3-(N-(pyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;99%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

4-(chlorosulfonyl)benzenesulfonyl fluoride

4-(chlorosulfonyl)benzenesulfonyl fluoride

4-(N-(pyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

4-(N-(pyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;99%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

4-chloro-2-methylquinoline
4295-06-1

4-chloro-2-methylquinoline

C14H12N4

C14H12N4

Conditions
ConditionsYield
With C51H57ClNiO2P2; sodium t-butanolate at 25℃;99%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With calcium carbonate In toluene at 20 - 65℃;
Stage #2: With water; sodium hydroxide In toluene at 100 - 115℃;
Stage #3: With acetic acid pH=5 - 5.5; Reagent/catalyst;
98.5%
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;
Stage #2: With sodium hydroxide for 2h; Inert atmosphere; Reflux;
65%
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h;
Stage #2: With sodium hydroxide for 2h; Reflux;
2-aminopyrimidine
109-12-6

2-aminopyrimidine

potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

cis-[bis(2-aminopyrimidine)-dichloro-platinum]
60185-34-4, 64440-33-1, 82371-67-3

cis-[bis(2-aminopyrimidine)-dichloro-platinum]

Conditions
ConditionsYield
In water for 48h; Darkness;98.36%
In water byproducts: KCl; addn. of pyrimidine soln. to Pt complex soln. (Pt:pyrimidine = 1:4), room temp.; holding, 10-12h; pptn.; filtration; repeated washing (water); drying (80°C);
2-aminopyrimidine
109-12-6

2-aminopyrimidine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E)-N,N-dimethyl-N'-(pyrimidin-2-yl)formimidamide

(E)-N,N-dimethyl-N'-(pyrimidin-2-yl)formimidamide

Conditions
ConditionsYield
In toluene for 6h; Reflux;98%
at 60 - 70℃; Condensation;
In toluene for 2h;88 mg
2-aminopyrimidine
109-12-6

2-aminopyrimidine

ibuprofen
15687-27-1

ibuprofen

2-(4-isobutyl-phenyl)-N-pyrimidin-2-yl-propionamide

2-(4-isobutyl-phenyl)-N-pyrimidin-2-yl-propionamide

Conditions
ConditionsYield
Stage #1: ibuprofen With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h;
Stage #2: 2-aminopyrimidine In dichloromethane for 72h; Heating;
98%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

bromobenzene
108-86-1

bromobenzene

phenyl-pyrimidin-2-yl-amine
57356-49-7

phenyl-pyrimidin-2-yl-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; for 18h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;98%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 100℃; for 22h;78%
With potassium tert-butylate In dimethyl sulfoxide at 120℃; for 12h;72%
With copper(l) iodide; potassium tert-butylate In 1,4-dioxane at 130℃; for 24h; Ullmann Condensation; Sealed tube; Inert atmosphere;42%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

6-amino-1,3-dimethyl-5-[(2-pyrimidyl)diazenyl]uracil
1242060-34-9

6-amino-1,3-dimethyl-5-[(2-pyrimidyl)diazenyl]uracil

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine With sulfuric acid; acetic acid; sodium nitrite at 0 - 5℃; for 2h;
Stage #2: 6-Amino-1,3-dimethylbarbituric acid With sodium hydroxide In water at 0 - 5℃; for 0.25h; pH=7;
98%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

N-(4-chlorobenzyl)-(2-pyrimidyl)amine
23676-57-5

N-(4-chlorobenzyl)-(2-pyrimidyl)amine

Conditions
ConditionsYield
With [RuCl(CO)(PPh3)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;98%
With [N,S-(2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone)RuH(CO)(PPh3)2]; potassium hydroxide In toluene at 100℃; for 12h; Reagent/catalyst;97%
With C41H36AsClN3OPRuS; potassium hydroxide In toluene at 100℃; for 12h;97%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

N-([1,1'-biphenyl]-2-yl)pyrimidin-2-amine
1372776-06-1

N-([1,1'-biphenyl]-2-yl)pyrimidin-2-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 95℃; for 18h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;98%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

phenyl-pyrimidin-2-yl-amine
57356-49-7

phenyl-pyrimidin-2-yl-amine

Conditions
ConditionsYield
With SingaCycle-A1; potassium hexamethylsilazane In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere;98%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

2-pyrimidine
16699-12-0

2-pyrimidine

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;97%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

parabanic acid
120-89-8

parabanic acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

2-(4-methoxyphenyl)-N3-[(E)-1-(4-methoxyphenyl)methylidene]imidazo[1,2-a]pyrimidin-3-amine
1089671-87-3

2-(4-methoxyphenyl)-N3-[(E)-1-(4-methoxyphenyl)methylidene]imidazo[1,2-a]pyrimidin-3-amine

Conditions
ConditionsYield
at 200℃; for 0.0833333h;97%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

parabanic acid
120-89-8

parabanic acid

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

2-(3-methylphenyl)-N3-[(E)-1-(3-methylphenyl)methylidene]imidazo[1,2-a]pyrimidin-3-amine
1089671-86-2

2-(3-methylphenyl)-N3-[(E)-1-(3-methylphenyl)methylidene]imidazo[1,2-a]pyrimidin-3-amine

Conditions
ConditionsYield
at 200℃; for 0.0833333h;97%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

β-naphthol
135-19-3

β-naphthol

1-(p-methylphenyl(2-pyrimidinylamino)methyl)naphthalene-2-ol
1094443-80-7

1-(p-methylphenyl(2-pyrimidinylamino)methyl)naphthalene-2-ol

Conditions
ConditionsYield
In water at 20℃; for 0.416667h;97%
at 125℃; for 0.05h; Mannich reaction; Neat (no solvent);92%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

β-naphthol
135-19-3

β-naphthol

1-[2-methoxyphenyl((pyrimidin-2-yl)amino)methyl]naphthalen-2-ol
1190380-97-2

1-[2-methoxyphenyl((pyrimidin-2-yl)amino)methyl]naphthalen-2-ol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,2-dichloro-ethane for 3h; Reflux;97%

109-12-6Relevant articles and documents

-

Chmelewskii

, (1956)

-

-

Lechowski

, p. 479 (1969)

-

Degradation of sulfadiazine antibiotics by water falling film dielectric barrier discharge

Rong, Shao-Peng,Sun, Ya-Bing,Zhao, Ze-Hua

, p. 187 - 192 (2014)

A new water falling film dielectric barrier discharge was applied to the degradation of sulfadiazine in the aqueous solution. The various parameters that affect the degradation of sulfadiazine and the proposed evolutionary process were investigated. The results indicated that the inner concentrations of 10 mg/L sulfadiazine can be all removed within 30 min. The optimum pH value was 9.10 and both strong acidic and alkaline solution conditions were not suitable for the degradation. The degradation of sulfadiazine can be enhanced by the addition of hydrogen radical scavengers, but be inhibited by adding hydroxyl radical scavengers. The water falling film dielectric barrier discharge was rather ineffective in mineralization, because of the intermediates were recalcitrant to be degraded. The existence of Fe2+ and CCl 4 in the liquid phase can promote the degradation and mineralization of sulfadiazine. It was found that the degradation of SDZ was enhanced by CCl4 was mainly because of the increase of OH due to the reaction of CCl4 with H that reduce the chances of their recombination with OH. Based on the 8 intermediate products identified by LC-MS, the proposed evolution of the degradation process was investigated.

-

Price,Moos

, p. 207 (1945)

-

C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Ham, Won Seok,Choi, Hoonchul,Zhang, Jianbo,Kim, Dongwook,Chang, Sukbok

supporting information, p. 2885 - 2892 (2022/02/23)

Synthesis of heteroaryl amines has been an important topic in organic chemistry because of their importance in small-molecule discovery. In particular, 2-Aminopyrimidines represent a highly privileged structural motif that is prevalent in bioactive molecules, but a general strategy to introduce the pyrimidine C2-N bonds via direct functionalization is elusive. Here we describe a synthetic platform for site-selective C-H functionalization that affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products in situ. Mechanism-based reagent design allowed for the C2-selective amination of pyrimidines, opening the new scope of site-selective heteroaryl C-H functionalization. Our method is compatible with a broad range of pyrimidines with sensitive functional groups and can access complex aminopyrimidines with high selectivity.

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.

supporting information, p. 482 - 487 (2019/01/04)

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles [1]

Al-Awadi, Sundus A.,Ibrahim, Maher R.,El-Dusouqui, Osman M. E.,Al-Awadi, Nouria A.

, p. 1812 - 1816 (2015/11/09)

Gas-phase pyrolysis of N-arylidine-N′-pyrimidin-2-yl-hydrazine derivatives 1a, 1b, 1c, 1d, 1e gave the corresponding arylnitriles 2a, 2b, 2c, 2d, 2e, 2-aminopyrimidine 3, 3-phenyl-1,2,4-triazolo[4,3-a]pyrimidines 4, 2-phenyl-1,2,4-triazolo[1,5-a]pyrimidines 5, 2,4,5-triphenyl-1H-imidazole 6, and 2,3-diphenylquinoline 7. The analyses of the reaction products are reported and used to elucidate the mechanism of the pyrolytic process.

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