6-Amino-1-methyluracil 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.

form 

powder to crystal

pka

9.26±0.40(Predicted)

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Amino-1-methyluracil Usage And Synthesis

Chemical Properties

almost white to slightly beige crystalline powder

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?(1?H,3H,3?H,7?H,1?H)-pentaone, via reaction with isatin in the presence of catalytic p-toluene sulfonic acid.

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.

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

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

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