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| | 2,4-Diamino-6-hydroxypyrimidine Basic information |
| Product Name: | 2,4-Diamino-6-hydroxypyrimidine | | Synonyms: | 2,4-Diamino-6-hydroxypyrimidine,96%;TIMTEC-BB SBB004252;2,4-DIAMINOPYRIMIDIN-6-OL;2,4-DIAMINO-6-HYDROXYPYRIMIDINE;2,4-DIAMINO-6-PYRIMIDINOL;2,4-DIAMINO-6(1H)-PYRIMIDINONE;2,6-DIAMINO-4-PYRIMIDINONE;2,6-DIAMINO-4(1H)-PYRIMIDINONE | | CAS: | 56-06-4 | | MF: | C4H6N4O | | MW: | 126.12 | | EINECS: | 200-254-4 | | Product Categories: | Pyrimidines;Building Blocks;PYRIMIDINE;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;APIs & Intermediate;Pyridines, Pyrimidines, Purines and Pteredines;Chemical Amines;13C & 2H Sugars;Amines;Bases & Related Reagents;Heterocycles;Nucleotides;Carbohydrates & Derivatives;bc0001;56-06-4 | | Mol File: | 56-06-4.mol |  |
| | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-36-26 | | WGK Germany | 3 | | Hazard Note | Irritant | | TSCA | TSCA listed | | HS Code | 29335995 |
| | 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 | 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 | | Uses | 2,4-Diamino-6-hydroxypyrimidine (cas# 56-06-4) is a compound useful in organic synthesis. | | 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] | | 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.]
| | References | [1] Patent: CN107857734, 2018, A. Location in patent: Paragraph 0032; 0033; 0034; 0035 |
| | 2,4-Diamino-6-hydroxypyrimidine Preparation Products And Raw materials |
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