3977-23-9

Basic information

• Product Name: 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE
• Synonyms: 2-AMINO-5,6-DIMETHYLPYRIMIDIN-4-OL;2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE;2-AMINO-5,6-DIMETHYL-4-PYRIMIDINOL;BUTTPARK 11\02-61;2-amino-5,6-dimethyl-1H-pyrimidin-4-one;4(1H)-Pyrimidinone, 2-amino-5,6-dimethyl- (9CI);2-Amino-5,6-dimethylpyrimidin-4(1H)-one;2-azanyl-5,6-dimethyl-1H-pyrimidin-4-one
• CAS NO: 3977-23-9
• Molecular Formula: C₆H₉N₃O
• Molecular Weight: 139.16
• EINECS: 223-611-6
• Product Categories: PYRIMIDINE;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 3977-23-9.mol

Chemical Properties

• Melting Point: 333-337 °C(lit.)
• Boiling Point: 341°C
• Flash Point: 110.4 °C
• Appearance: White/Powder
• Density: 1.36 g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.625
• PKA: 10.18±0.50(Predicted)
• CAS DataBase Reference: 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE(3977-23-9)
• EPA Substance Registry System: 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE(3977-23-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3977-23-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5,6-Dimethyl-4-Hydroxypyrimidine is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, 2-Amino-5,6-Dimethyl-4-Hydroxypyrimidine serves as a valuable compound for studying the properties and reactions of aminopyrimidines. Researchers can use 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE to explore new synthetic routes, investigate its reactivity, and understand its potential applications in various chemical processes.
Used in Agrochemical Industry:
2-Amino-5,6-Dimethyl-4-Hydroxypyrimidine may also find applications in the agrochemical industry, where it could be used as a starting material for the synthesis of pesticides, herbicides, or other agrochemical products. Its potential use in this industry would depend on its effectiveness and safety profile in controlling pests and weeds while minimizing harm to the environment and non-target organisms.
Used in Material Science:
In material science, 2-Amino-5,6-Dimethyl-4-Hydroxypyrimidine could be explored for its potential use in the development of new materials with unique properties. Its incorporation into polymers or other materials could lead to the creation of novel materials with enhanced properties, such as improved stability, reactivity, or selectivity in various applications.

InChI:InChI=1/C6H9N3O/c1-3-4(2)8-6(7)9-5(3)10/h1-2H3,(H3,7,8,9,10)

Upstream product

• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 50-01-1 guanidine hydrochloride 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 594-14-9 guanidinium sulfate 
• 593-85-1 diguanidine carbonate 

Downstream Products

• 14394-61-7 2-amino-4-chloro-5,6-dimethyl-pyrimidine 
• 857621-81-9 N-acetyl-sulfanilic acid-(4-methoxy-5,6-dimethyl-pyrimidin-2-ylamide) 

Relevant articles and documents

3-Ethyl-6-methyl-isocytosines: Synthesis and solid state structural analysis

The syntheses and solid state structures of 3-ethyl-6- methyl-5-alkyl-isocytosines (alkyl=H, Me, Et, n-Pr, n-Bu) are presented. These heterocycles consistently self-assemble into N-H N hydrogen-bonded dimers, which further associate by N-H···O=C interactions, or N-H···O-H···O=C hydrogen bonds involving water of crystallization, generating extended supramolecular networks. Crystal packing analysis indicates that although hydrogen bonding is the primary intermolecular interaction in these molecular crystals, the dispersion forces may play a decisive role in determining their final three-dimensional arrangements. (C) 2000 Elsevier Science Ltd.

Discovery and SAR of 6-alkyl-2,4-diaminopyrimidines as histamine H 4 receptor antagonists

This report discloses the discovery and SAR of a series of 6-alkyl-2-aminopyrimidine derived histamine H4 antagonists that led to the development of JNJ 39758979, which has been studied in phase II clinical trials in asthma and atopic dermatitis. Building on our SAR studies of saturated derivatives from the indole carboxamide series, typified by JNJ 7777120, and incorporating knowledge from the tricyclic pyrimidines led us to the 6-alkyl-2,4-diaminopyrimidine series. A focused medicinal chemistry effort delivered several 6-alkyl-2,4-diaminopyrimidines that behaved as antagonists at both the human and rodent H4 receptor. Further optimization led to a panel of antagonists that were profiled in animal models of inflammatory disease. On the basis of the preclinical profile and efficacy in several animal models, JNJ 39758979 was selected as a clinical candidate; however, further development was halted during phase II because of the observation of drug-induced agranulocytosis (DIAG) in two subjects.