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56-06-4

Basic Information
CAS No.: 56-06-4
Name: 2,4-Diamino-6-hydroxypyrimidine
Article Data: 16
Molecular Structure:
Molecular Structure of 56-06-4 (2,4-Diamino-6-hydroxypyrimidine)
Formula: C4H6N4O
Molecular Weight: 126.118
Synonyms: 4(1H)-Pyrimidinone,2,6-diamino- (8CI,9CI);2,4-Diamino-6-hydroxypyrimidine;2,4-Diamino-6-pyrimidinone;2,6-Diamino-3,4-dihydropyrimidin-4-one;2,6-Diamino-4(1H)-pyrimidinone;2,6-Diamino-4(3H)-pyrimidinone;2,6-Diamino-4-hydroxypyrimidine;2,6-Diamino-4-pyrimidinol;2,6-Diaminopyrimidin-4-one;2,6-Diaminopyrimidine-4(3H)-one;6-Aminoisocytosine;6-Hydroxy-2,4-pyrimidinediamine;NSC 44914;NSC 680818;NSC9302;
EINECS: 200-254-4
Density: 1.84 g/cm3
Melting Point: 285-286 °C (dec.)(lit.)
Boiling Point: 288.5 °C at 760 mmHg
Flash Point: 128.3 °C
Appearance: white solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
PSA: 98.05000
LogP: 0.50900
Synthetic route
506-93-4

guanidine nitrate

105-56-6

ethyl 2-cyanoacetate

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
Stage #1: guanidine nitrate; ethyl 2-cyanoacetate With sodium methylate In methanol for 4h; Reflux;
Stage #2: With hydrogenchloride In water pH=9; pH-value;
95%
113-00-8

guanidine nitrate

105-56-6

ethyl 2-cyanoacetate

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
With triethylamine In ethanol for 4h; Reflux;66%
88075-70-1

2,4-diamino-5-formyl-6-oxo(1H)-pyrimidine

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
With sulfuric acid In methanol for 72h; Ambient temperature;
108-98-5

thiophenol

A

831-91-4

Benzyl phenyl sulfide

B

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
With triethylamine In methanol at 60℃; Rate constant;
696-83-3

2,4-diamino-6-fluoropyrimidine

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; Rate constant;

A

51953-18-5

pyrimidine-4(3H)-one

B

156-81-0

2,4-diaminopyrimidine

C

120-89-8

parabanic acid

D

108-53-2

isocytosine

E

71-30-7

Cytosine

F

144-62-7

oxalic acid

G

113-00-8

guanidine nitrate

H

127-17-3

2-oxo-propionic acid

I

66-22-8

uracil

J

56-06-4

2,6-diaminopyrimidin-4-ol

L

57-13-6

urea

M

56-40-6

glycine

Conditions
ConditionsYield
With copper(II) choride dihydrate In water at 80℃; for 24h; pH=7.57;A 5.6 mg
B 0.3 mg
C 0.59 mg
D 5 mg
E 0.13 mg
F 0.1 mg
G 1.6 mg
H 0.0018 mg
I 3.8 mg
J 0.3 mg
K 0.01 mg
L 1.7 mg
M 0.76 mg

A

51953-18-5

pyrimidine-4(3H)-one

B

156-81-0

2,4-diaminopyrimidine

C

113-00-8

guanidine nitrate

D

66-22-8

uracil

E

56-06-4

2,6-diaminopyrimidin-4-ol

F

57-13-6

urea

Conditions
ConditionsYield
With manganese(II) chloride tetrahydrate In water at 80℃; for 24h; pH=7.57;A 0.3 mg
B 0.02 mg
C 0.1 mg
D 0.03 mg
E 0.06 mg
F 0.005 mg
506-93-4

guanidine nitrate

105-34-0

methyl 2-cyanoacetate

56-06-4

2,6-diaminopyrimidin-4-ol

Conditions
ConditionsYield
With sodium methylate

A

51953-18-5

pyrimidine-4(3H)-one

B

1455-77-2

guanazole

C

120-89-8

parabanic acid

D

849585-22-4

LACTIC ACID

E

73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

F

328-42-7

Oxalacetic acid

G

2491-15-8

formylglycine

H

110-15-6

succinic acid

I

71-30-7

Cytosine

J

120-73-0

purine

K

144-62-7

oxalic acid

L

113-00-8

guanidine nitrate

M

127-17-3

2-oxo-propionic acid

N

66-22-8

uracil

O

56-06-4

2,6-diaminopyrimidin-4-ol

Q

57-13-6

urea

R

56-40-6

glycine

S

302-72-7

rac-Ala-OH

T

18588-61-9

2,4-diamino-pyrimidine-5-carboxylic acid

U

isocytosine

Conditions
ConditionsYield
With ferric sulfate nonahydrate; water at 80℃; for 24h;

B

1455-77-2

guanazole

C

849585-22-4

LACTIC ACID

D

328-42-7

Oxalacetic acid

E

110-15-6

succinic acid

F

120-73-0

purine

G

144-62-7

oxalic acid

H

66-22-8

uracil

I

56-06-4

2,6-diaminopyrimidin-4-ol

J

57-13-6

urea

Conditions
ConditionsYield
With copper(II) chloride tetrahydrate; water at 80℃; for 24h;
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Specification

The IUPAC name of 2,4-Diamino-6-hydroxypyrimidine is 2,6-diamino-1H-pyrimidin-4-one. With the CAS registry number 56-06-4, it is also named as 4(1H)-Pyrimidinone, 2,6-diamino-. The product's categories are Pyrimidine; APIs & Intermediate; Pyridines, Pyrimidines, Purines and Pteredines; Chemical Amines; 13C & 2H Sugars; Amines; Bases & Related Reagents; Heterocycles; Nucleotides; Carbohydrates & Derivatives, and the other registry numbers are 40306-60-3; 41982-31-4; 863767-89-9. Besides, it is white solid, which should be stored in sealed, dark, cool, ventilated and dry place away from fire and heat source. In addition, it is light sensitive.

The other characteristics of this product can be summarized as: (1)EINECS: 200-254-4; (2)ACD/LogP: -1.66; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -1.66; (5)ACD/LogD (pH 7.4): -1.66; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 2.95; (9)ACD/KOC (pH 7.4): 2.98; (10)H bond acceptors: 5; (11)H bond donors: 5; (12)Freely Rotating Bonds: 1; (13)Index of Refraction: 1.798; (14)Molar Refractivity: 29.21 cm3; (15)Molar Volume: 68.4 cm3; (16)Surface Tension: 94.7 dyne/cm; (17)Density: 1.84 g/cm3; (18)Flash Point: 128.3 °C; (19)Melting point: 285-286 °C; (20)Enthalpy of Vaporization: 52.78 kJ/mol; (21)Boiling Point: 288.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00232 mmHg at 25 °C.

Preparation of 2,4-Diamino-6-hydroxypyrimidine: please put Guanidine nitrate in the solution of Sodium methoxide (or 50% NaOH) to heat and stir. After backflow half-hour, please drop Methyl cyanoacetate to reflow 2 hours. After the reaction complete, please heat the reclaimed Methanol. And then put the residues in the hot water to dissolve. When the temperature reach 80 °C, please add acetic acid to adjust pH=8. Then please separate crystallographic product out. After cooling below 20 °C, you would get this chemical by filtration, washing and drying.

Uses of 2,4-Diamino-6-hydroxypyrimidine: it is used for detection of nitrate and nitrite. It is also used in organic synthesis and pharmaceutical intermediates. And it is used for the production of AZM, minoxidilum and olic acid. Furthermore, it can react with 1,3-Dichloro-propan-2-one to get 5-Chloromethyl-furo[2,3-d]pyrimidine-2,4-diamine.



This reaction needs Dimethylformamide at temperature of 20 °C for 24 hours. The yield is 80 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. Please do not breathe dust. And please avoid contact with skin and eyes. You should wear suitable protective clothing. Moreover, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C/1/N=C(/N)NC(\N)=C\1
(2)InChI:InChI=1/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)
(3)InChIKey:SWELIMKTDYHAOY-UHFFFAOYAR
(4)Std. InChI:InChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)
(5)Std. InChIKey:SWELIMKTDYHAOY-UHFFFAOYSA-N

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