2,4-Diamino-6-hydroxypyrimidine Chemical Properties

Melting point:

285-286 °C (dec.) (lit.)

Boiling point:

234.22°C (rough estimate)

Density 

1.3659 (rough estimate)

refractive index 

1.7990 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.61±0.50(Predicted)

form 

Fine Crystalline Powder

color 

White to cream

Sensitive 

Light Sensitive

Merck 

14,2981

BRN 

125006

InChIKey

SWELIMKTDYHAOY-UHFFFAOYSA-N

CAS DataBase Reference

56-06-4(CAS DataBase Reference)

NIST Chemistry Reference

4(1H)-pyrimidinone, 2,6-diamino-(56-06-4)

EPA Substance Registry System

2,6-Diamino-4(1H)-pyrimidinone (56-06-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29335995

MSDS

• Language:English Provider:2,4-Diamino-6-hydroxypyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4-Diamino-6-hydroxypyrimidine Usage And Synthesis

Description

2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC₅₀ for inhibition of BH₄ biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.

Chemical Properties

White Solid

Uses

2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC50 for inhibition of BH4 biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.[Cayman Chemical]

Uses

2,4-Diamino-6-hydroxypyrimidine (cas# 56-06-4) is a compound useful in organic synthesis.

Uses

It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan

Synthesis

A solution of sodium ethoxide is prepared from 23 g. (1 g. atom) of sodium and 250 ml of anhydrous ethanol in a 1-l round-bottomed flask fitted with a reflux condenser carrying a calcium chloride drying tube. After the sodium has dissolved, the solution is cooled and 113 g. (1 mole) of ethyl cyanoacetate is added. This mixture is allowed to stand while a second solution of sodium ethoxide of the same volume and concentration is prepared. To this solution is added 97 g. (1.02 moles) of guanidine hydrochloride. The sodium chloride is separated by filtration, and the clear filtrate containing guanidine is added to the solution of ethyl sodiocyanoacetate. This mixture is heated for 2 hours under reflux and is then evaporated to dryness at atmospheric pressure. The solid product is dissolved in 325 ml. of boiling water and acidified with 67 ml. of glacial acetic acid. Upon cooling of the solution, 101–103 g. (80–82%) of yellow needles separates; m.p. 260–270° (dec.)

storage

+4°C

Purification Methods

2,4-Diamino-6-hydroxypyrimidine recrystallises from H2O. [Beilstein 25 III/IV 3642.]

2,4-Diamino-6-hydroxypyrimidine(56-06-4)Related Product Information

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• PeMetrexed IMpurity D
• PeMetrexed EP IMpurity C
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