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2,4-Diamino-6-hydroxypyrimidine

2,4-Diamino-6-hydroxypyrimidine ??? ???
?? ??:
56-06-4
???:
2,4-Diamino-6-hydroxypyrimidine
???(??):
1956-6-4;2,6-DIAMINOPYRIMIDIN-4-OL;DAHP;2,6-Diaminopyrimidin-4(1H)-one;2,6-DIAMINO-4-PYRIMIDINOL;2,6-diamino-1H-pyrimidin-4-one;2,6-DIAMINO-4-HYDROXYPYRIMIDINE;4(3H)-pyrimidinone, 2,6-diamino-;9-60-9;NSC 9302
CBNumber:
CB0174912
???:
C4H6N4O
??? ??:
126.12
MOL ??:
56-06-4.mol
MSDS ??:
SDS

2,4-Diamino-6-hydroxypyrimidine ??

???
285-286 °C (dec.) (lit.)
?? ?
234.22°C (rough estimate)
??
1.3659 (rough estimate)
???
1.7990 (estimate)
?? ??
Keep in dark place,Inert atmosphere,Room temperature
???
DMSO(?? ???), ???(?? ???)
?? ?? (pKa)
10.61±0.50(Predicted)
??? ??
?? ??? ??
??
???? ?????
??
Light Sensitive
Merck
14,2981
BRN
125006
InChIKey
SWELIMKTDYHAOY-UHFFFAOYSA-N
CAS ??????
56-06-4(CAS DataBase Reference)
NIST
4(1H)-pyrimidinone, 2,6-diamino-(56-06-4)
EPA
2,6-Diamino-4(1H)-pyrimidinone (56-06-4)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi
?? ???? ?? 36/37/38
????? 22-24/25-36-26
WGK ?? 3
?? ?? ?? Irritant
TSCA Yes
HS ?? 29335995
???? ?? KE-09742
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
??????:
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P280 ????/???/???/?????? ?????.
NFPA 704
1
2 0

2,4-Diamino-6-hydroxypyrimidine MSDS


2,4-Diamino-6-hydroxypyrimidine

2,4-Diamino-6-hydroxypyrimidine C??? ??, ??, ??

??

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.

??? ??

White Solid

??

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]

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.) 2,4-Diamino-6-hydroxypyrimidine synthesis route

Purification Methods

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

2,4-Diamino-6-hydroxypyrimidine ?? ?? ? ???

???

?? ??


2,4-Diamino-6-hydroxypyrimidine ?? ??

???( 549)?? ??
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2,4-Diamino-6-hydroxypyrimidine ?? ??:

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