ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Urine (urea) pyrimidine 6-Amino-1-methyluracil

6-Amino-1-methyluracil

Product Name6-Amino-1-methyluracil
CAS2434-53-9
MFC5H7N3O2
MW141.13
EINECS219-422-3
MOL File2434-53-9.mol

Chemical Properties

Melting point	300 °C
Density	1.339±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	Soluble in diluted sodium hydroxide solution.
pka	9.26±0.40(Predicted)
form	powder to crystal
color	White to Almost white
BRN	127771
InChI	InChI=1S/C5H7N3O2/c1-8-3(6)2-4(9)7-5(8)10/h2H,6H2,1H3,(H,7,9,10)
InChIKey	GZLZRPNUDBIQBM-UHFFFAOYSA-N
SMILES	C1(=O)N(C)C(N)=CC(=O)N1
CAS DataBase Reference	2434-53-9(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	22-36/37/38
Safety Statements	26
WGK Germany	3
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

almost white to slightly beige crystalline powder

Uses

6-Amino-1-methyluracil is known to exert inhibitory effects towards DNA repair glycosylase. It is also known to be used as a flame retardant.

Uses

6-Amino-1-methyluracil may be used in the preparation of 1,1-di methyl-1H-spiro[pyrimido[4,5-b]quinoline-5,5-pyrrolo[2,3-d]pyrimidine]-2,2,4,4,6(1H,3H,3H,7H,1H)-pentaone, via reaction with isatin in the presence of catalytic p-toluene sulfonic acid.

General Description

6-Amino-1-methyluracil is an amino derivative of uracil and its standard molar enthalpy of combustion has been evaluated. Host-guest complexation of 6-amino-1-methyluracil with tetrapropoxycalix[4]arene has been reported.

Synthesis

105-56-6

598-50-5

2434-53-9

GENERAL METHOD: Ethyl cyanoacetate (0.1 mol) was mixed with N-methylurea (0.1 mol) in anhydrous ethanol (290 mL) containing sodium, and the reaction was carried out with reference to literature methods 26-34. The reaction mixture was refluxed for 10-12 hours and subsequently cooled to room temperature. Acidification was carried out by adjusting the pH to 6 with acetic acid. The resulting precipitate was washed with distilled water and dried in a desiccator overnight.

References

[1] Journal of Medicinal Chemistry, 1999, vol. 42, # 13, p. 2344 - 2350
[2] RSC Advances, 2015, vol. 5, # 28, p. 21464 - 21470
[3] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 4, p. 477 - 482
[4] Journal of Chemical Research, 2016, vol. 40, # 12, p. 771 - 777
[5] Patent: EP3299371, 2018, A1. Location in patent: Paragraph 0587; 0588

6-Amino-1-methyluracil

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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