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171887-03-9

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171887-03-9 Usage

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 171887-03-9 differently. You can refer to the following data:
1. N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide (Abacavir - In House Impurity) is an intermediate of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.
2. Abacavir intermediate. A purine derivative

Check Digit Verification of cas no

The CAS Registry Mumber 171887-03-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,1,8,8 and 7 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 171887-03:
(8*1)+(7*7)+(6*1)+(5*8)+(4*8)+(3*7)+(2*0)+(1*3)=159
159 % 10 = 9
So 171887-03-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H4Cl2N4O/c6-3-2(9-1-12)4(7)11-5(8)10-3/h1H,(H,9,12)(H2,8,10,11)

171887-03-9SDS

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 N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide

1.2 Other means of identification

Product number -
Other names N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

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:171887-03-9 SDS

171887-03-9Synthetic route

2-nitroso-4,6-dichloro-5-formamidopyrimidine

2-nitroso-4,6-dichloro-5-formamidopyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 40℃; under 7500.75 - 11251.1 Torr; for 4h; Temperature; Autoclave;98%
formic acid
64-18-6

formic acid

2,5-diamino-4,6-dichloropyrimidine
55583-59-0

2,5-diamino-4,6-dichloropyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
Stage #1: formic acid; 2,5-diamino-4,6-dichloropyrimidine at 50 - 55℃; for 3h;
Stage #2: In toluene at 50℃; under reduced pressure;
90%
2,5-diamino-4,6-dihydroxypyrimidine hydrochloride

2,5-diamino-4,6-dihydroxypyrimidine hydrochloride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With thionyl chloride; trichlorophosphate at 80℃; for 2.5h; Temperature;82.6%
2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine
171887-02-8

2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
In phosphate buffer for 4h; pH=3.2; Hydrolysis; Heating;72%
2-Amino-4,6-dichloro-5-[(dimethylamino)methyleneamino]pyrimidine

2-Amino-4,6-dichloro-5-[(dimethylamino)methyleneamino]pyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With potassium dihydrogenphosphate; phosphoric acid In chloroform methanol68%
2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride
56830-58-1

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 50℃; for 0.75h;
Stage #2: 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride at 70 - 90℃; for 17.45 - 20.45h;
Stage #3: With sodium hydroxide; water at 20 - 97℃; for 4 - 8h; pH=0.5 - 4.0; Product distribution / selectivity;
37.4%
4,6-Dichloro-2,5-bis-[(dimethylamino)methyleneamino]pyrimidine

4,6-Dichloro-2,5-bis-[(dimethylamino)methyleneamino]pyrimidine

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride
56830-58-1

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With sodium hydroxide; phosphoric acid; trichlorophosphate In N-methyl-acetamide; water; toluene
2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride
56830-58-1

2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With sodium hydroxide; trichlorophosphate In N-methyl-acetamide; water
With sodium hydroxide; trichlorophosphate In N-methyl-acetamide; water
2,5-bis{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine
171887-01-7

2,5-bis{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With sodium hydroxide; phosphoric acid; water at 100℃; for 4h; pH=4; Product distribution / selectivity;
2,5-diamino-4,6-dichloropyrimidine
55583-59-0

2,5-diamino-4,6-dichloropyrimidine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

Conditions
ConditionsYield
With formic acid In water; toluene
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

4-[2-amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester
1435953-79-9

4-[2-amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;100%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 1h;100%
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

7-chlorothiazolo[5,4-d]pyrimidin-5-amine
1211527-74-0

7-chlorothiazolo[5,4-d]pyrimidin-5-amine

Conditions
ConditionsYield
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;93.4%
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;93.4%
With Lawessons reagent In tetrahydrofuran at 65℃; for 0.5h;93.4%
(3-methyl-4-nitrophenyl)methanamine hydrochloride
1037397-91-3

(3-methyl-4-nitrophenyl)methanamine hydrochloride

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

N-[2-amino-4-chloro-6-(3-methyl-4-nitro-benzylamino)-pyrimidin-5-yl]-formamide
1040353-71-6

N-[2-amino-4-chloro-6-(3-methyl-4-nitro-benzylamino)-pyrimidin-5-yl]-formamide

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 58 - 65℃; for 3.5 - 4.66667h; Heating / reflux;92%
((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
171887-04-0

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions
ConditionsYield
Stage #1: ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate With sodium carbonate In isopropyl alcohol at 20℃; for 1h;
Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In isopropyl alcohol Concentration; Solvent; Reflux;
88.2%
(1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

(1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

C24H43ClFN5O3Si2

C24H43ClFN5O3Si2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 12h; Microwave irradiation;88%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 12h; Microwave irradiation;88%
(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene
136522-35-5

(1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
171887-04-0

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions
ConditionsYield
With triethylamine In ethanol; water85%
With triethylamine In ethanol for 7h; Substitution; Heating;83%
With sodium hydroxide; triethylamine In acetic acid 1-hydroxy-propyl ester; ethanol
Stage #1: (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With triethylamine In industrial methylated spirit; water for 17h; Heating / reflux;
Stage #2: With potassium carbonate In industrial methylated spirit at 25 - 30℃; for 0.5h;
Stage #3: In industrial methylated spirit at 0 - 5℃; Product distribution / selectivity;
Stage #1: (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With sodium hydrogencarbonate In idustrial methylated spirit; water for 4h; Heating / reflux;
Stage #2: In industrial methylated spirit at -5℃; for 1h; Product distribution / selectivity;
((1R*,3R*,4R*)-3-aminobicyclo[2.2.1]heptan-1-yl)methanol

((1R*,3R*,4R*)-3-aminobicyclo[2.2.1]heptan-1-yl)methanol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

[(1R*,3R*,4R*)-3-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

[(1R*,3R*,4R*)-3-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 140℃; for 1h; Microwave irradiation; Sealed tube;83%
(4-aminobicyclo[2.2.1]hept-1-yl)methanol

(4-aminobicyclo[2.2.1]hept-1-yl)methanol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

[4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

[4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;81%
4-aminobenzamide
2835-68-9

4-aminobenzamide

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

4-(2-amino-6-((4-carbamoylphenyl)amino)9H-purin-9-yl)benzamide

4-(2-amino-6-((4-carbamoylphenyl)amino)9H-purin-9-yl)benzamide

Conditions
ConditionsYield
In 1,4-dioxane; water Reflux;79%
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

2,5-diamino-4,6-dichloropyrimidine
55583-59-0

2,5-diamino-4,6-dichloropyrimidine

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 6h; Hydrolysis; Heating;77%
In hydrogenchloride; ethanol65%
((1R,2R,3S,4R)-4-amino-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

((1R,2R,3S,4R)-4-amino-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

((1R,2R,3S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

((1R,2R,3S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2,3-bis((tert-butyldimethylsilyl)oxy)cyclopentyl)methanol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 24h; Sealed tube;75%
With N-ethyl-N,N-diisopropylamine; butan-1-ol at 160℃; for 24h; Sealed tube;75%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 24h; Sealed tube;
(1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride

(1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
171887-04-0

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In 2-methyl-propan-1-ol74%
Stage #1: (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride With sodium hydrogencarbonate In isopropyl alcohol at 20℃; for 1h;
Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In isopropyl alcohol Concentration; Reagent/catalyst; Reflux;
51.4%
Stage #1: (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride With sodium hydrogencarbonate In ethanol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide In ethanol at 75 - 80℃; for 3h; Inert atmosphere;
(S)-(6-(((tetrahyd rofuran-3-yl)oxy)methyl)pyridin-2-yl)methanamine
1202402-79-6

(S)-(6-(((tetrahyd rofuran-3-yl)oxy)methyl)pyridin-2-yl)methanamine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

N-[2-amino-4-chloro-6-((6-[(S)-(tetrahydro-furan-3-yl)oxymethyl]pyridin-2-ylmethyl)amino)pyrimidin-5-yl]formamide
1202402-77-4

N-[2-amino-4-chloro-6-((6-[(S)-(tetrahydro-furan-3-yl)oxymethyl]pyridin-2-ylmethyl)amino)pyrimidin-5-yl]formamide

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol for 2h; Reflux;73%
(±)-cis-3-aminocyclopentanol

(±)-cis-3-aminocyclopentanol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

2-amino-6-chloro-9-(cis-3′-hydroxycyclopentyl)purine

2-amino-6-chloro-9-(cis-3′-hydroxycyclopentyl)purine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;72%
(1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

(1S,2R,3S,4R,5R)-4-[((1,1-dimethylethyl)dimethylsilyloxy)]-5-[((1,1-dimethylethyl)dimethyl-silyloxy)methyl]-3-fluorobicyclo[3.1.0]hexan-2-amine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

A

C24H43ClFN5O3Si2

C24H43ClFN5O3Si2

B

C24H41ClFN5O2Si2

C24H41ClFN5O2Si2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 160℃; for 2h; Microwave irradiation;A 70%
B 24%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Solvent; Microwave irradiation;A 59%
B 40%
(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
155899-66-4

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-2-amino-6-chloro-9H-purine

9-[(1′R,2′S,3′R,4′S)-4′-hydroxy-2′,3′-O-isopropylidene-cyclopentan-1′-yl]-2-amino-6-chloro-9H-purine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 120℃;66%
(1SR,2SR,4SR)-4-aminobicyclo[2.2.1]heptan-2-ol hydrochloride

(1SR,2SR,4SR)-4-aminobicyclo[2.2.1]heptan-2-ol hydrochloride

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]heptan-2-ol

4-(2-amino-6-chloro-9H-purin-9-yl)bicyclo[2.2.1]heptan-2-ol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Microwave irradiation;63%
C7H11N

C7H11N

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

C12H12ClN5
1621165-38-5

C12H12ClN5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;57%
4-pentylbicyclo[2.2.2]oct-1-ylamine

4-pentylbicyclo[2.2.2]oct-1-ylamine

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

C18H26ClN5
1621165-41-0

C18H26ClN5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 160℃; for 2h; Sealed tube; Microwave irradiation;57%
N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(3aS,4R,6R,6aR)-6-((methoxymethoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine
90597-13-0

(3aS,4R,6R,6aR)-6-((methoxymethoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

(1R,2S,3R,4R)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2,3-isopropylidenedioxy-4-(methoxymethoxymethyl)cyclopentane
1203452-14-5

(1R,2S,3R,4R)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2,3-isopropylidenedioxy-4-(methoxymethoxymethyl)cyclopentane

Conditions
ConditionsYield
With triethylamine In ethanol for 7h; Reflux;51.5%
(4R,3R,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

(4R,3R,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(4R,3R,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

(4R,3R,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

Conditions
ConditionsYield
Stage #1: (4R,3R,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 130℃; for 16h;
Stage #2: With hydrogenchloride In methanol at 60℃; for 16h;
48%
2-(6-(aminomethyl)pyridin-2-yl)propan-2-ol
1202403-02-8

2-(6-(aminomethyl)pyridin-2-yl)propan-2-ol

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

7-chloro-3-(6-[1-hydroxy-1-methylethyl]pyridine-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine
1202402-84-3

7-chloro-3-(6-[1-hydroxy-1-methylethyl]pyridine-2-ylmethyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine

Conditions
ConditionsYield
Stage #1: 2-(6-(aminomethyl)pyridin-2-yl)propan-2-ol; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With triethylamine In isopropyl alcohol at 90℃; for 4h;
Stage #2: With hydrogenchloride In ethanol; water at 90℃; for 2h;
Stage #3: With sodium nitrite In ethanol; water at 0℃;
47%
(4S,3S,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

(4S,3S,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

(4S,3S,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

(4S,3S,1R)-4-(guanin-9-yl)-3-hydroxy-1-hydroxymethylphospholane 1-oxide

Conditions
ConditionsYield
Stage #1: (4S,3S,1R)-4-amino-3-hydroxy-1-trityloxymethylphospholane 1-oxide; N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide With N-ethyl-N,N-diisopropylamine In butan-1-ol at 130℃; for 16h;
Stage #2: With hydrogenchloride In methanol at 60℃; for 16h;
45%
tert-butyl 5,8-diazaspiro[3.5]nonane-8-carboxylate
886766-31-0

tert-butyl 5,8-diazaspiro[3.5]nonane-8-carboxylate

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide
171887-03-9

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide

tert-butyl 9-(2-amino-6-chloro-5-formamidopyrimidin-4-yl)-6,9-diazaspiro[3.5]-nonane-6-carboxylate
1435953-91-5

tert-butyl 9-(2-amino-6-chloro-5-formamidopyrimidin-4-yl)-6,9-diazaspiro[3.5]-nonane-6-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 20h;22%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 168h;0.44 g

171887-03-9Relevant articles and documents

Preparation method of 2-amino-4, 6-dichloro-5-formamidopyrimidine

-

Paragraph 0054; 0062; 0067, (2020/12/30)

The invention provides a preparation method of 2-amino-4, 6-dichloro5formyl pyrimidine. The preparation method comprises the following steps: by taking malononitrile, formamidine or hydrochloride thereof as initial raw materials, carrying out nitrosation, formylation, cyclization, diazotization, Sandmeyer and reduction reaction to prepare the 2-amino-4, 6-dichloro-5-formamidopyrimidine. The preparation method disclosed by the invention is high in yield and high in product purity.

Method for Producing 2-Amino-4,6-Dichloro-5-Formamidopyrimidine

-

, (2008/06/13)

The invention relates to a method for producing 2-amino-4,6-dichloro-5-formamidopyrimidine from 2,5-diamino-4,6-dihydroxypyrimidine or a salt thereof. According to said method, a) 2,5-diamino-4,6-dihydroxypyrimidine or the salt or tautomer forms thereof are reacted with a chlorination agent and a formamide of formula (I) wherein R1 and R2 independently represent a C1-C4 alkyl radical or —R1-R2— represents —(CH2)n— where n=4-6, or —(CH2)2-0-(CH2)2—, without adding a solvent, at a temperature of between 50 and 130° C., b) the reaction product obtained in step a) is reacted with water at a temperature of between 0 and 100° C., and regulated to a pH value of between 1 and 6 with an inorganic base, and c) the aqueous reaction mixture obtained in step b) is left to react at a temperature of between 70 and 120° C. under hydrolysis to form 2-amino-4,6-dichloor-5-formamidopyrimidine. The inventive method enables satisfactory yields and high levels of purity of the end product to be obtained. As a result of the significantly reduced reaction volumes due to the solvent, auxiliary substances and residual substances saved, and the significantly simplified method, the costs incurred in the production of 2-amino-4,6-dichloro-5-formylaminopyrimidine are significantly reduced.

Process for the preparation of 2,5-diamino-4,6-dihalogenopyrimidinen

-

Page 5, (2008/06/13)

A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines of formula (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine of formula (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. X = halo.

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