6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Chemical Properties

Melting point:

295 °C (dec.) (lit.)

Boiling point:

243.1±43.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

6g/l

form 

Solid

pka

5.17±0.70(Predicted)

color 

Pale Beige

PH

6.9 (100g/l, H2O, 20℃)

Water Solubility 

7.06g/L(25 ºC)

InChIKey

VFGRNTYELNYSKJ-UHFFFAOYSA-N

LogP

-0.4 at 20℃

CAS DataBase Reference

6642-31-5(CAS DataBase Reference)

EPA Substance Registry System

2,4(1H,3H)-Pyrimidinedione, 6-amino-1,3-dimethyl- (6642-31-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

WGK Germany 

1

RTECS 

YQ8755000

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione Usage And Synthesis

Chemical Properties

Crystallizes (water). Melting point 295°C (293°C). Decomposes.

Uses

6-Amino-1,3-dimethyluracil is used as a reagent in the synthesis of new pyrimidine and caffeine derivatives that display highly potential antitumor activity. It is also used as a starting material in the synthesis of fused pyrido-pyrimidines.

Synthesis

General procedure for the synthesis of 1,3-dimethyl-6-aminouracil from 4-amino-2,6-dihydroxypyrimidine and iodomethane: 4-amino-2,6-dihydroxypyrimidine (1.27 g, 10 mmol) was added to a pre-heated ethanol solution (50 ml) containing KOH (0.56 g, 10 mmol) and heated continuously for 40 min. After completion of the reaction, the mixture was cooled to room temperature followed by addition of iodomethane (20 mmol). The reaction mixture was stirred under heating conditions for 8 hours, after which it was cooled to room temperature. The reaction mixture was poured into cold distilled water (100 ml) to induce precipitation of the final product 1,3-dimethyl-6-aminouracil. The precipitate was collected by filtration and washed with distilled water (100 ml). Finally, recrystallization from methanol gave 1,3-dimethyl-6-aminouracil in yellow crystalline form.

References

[1] Letters in Drug Design and Discovery, 2015, vol. 12, # 6, p. 471 - 478
[2] DRP/DRBP Org.Chem.,
[3] Patent: CN104744471, 2016, B. Location in patent: Paragraph 0026; 0027; 0028

6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione(6642-31-5)Related Product Information

• 1,3,7-TRIMETHYLURIC ACID
• aminometradine
• 1,3-Dimethylurea
• 6-AMINO-1,3-DIMETHYL-5-NITROSOURACIL
• 5,6-Diamino-1,3-dimethyluracil hydrate
• 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• 1,3-Dimethyluric acid
• 6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil
• TETRAMETHYLURIC ACID
• Semicarbazide
• 1,3-Dimethyluracil
• 6-Aminouracil
• 1,3-DIMETHYL-6-HYDRAZINOURACIL
• 6-AMINO-1,3-DIMETHYL-2,4-DIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE-5-CARBALDEHYDE
• 1,3-DIETHYL-5-NITROSO-6-AMINOURACIL
• 1,3-DIETHYL-5,6-DIAMINOURACIL
• 6-AMino-1-isobutyl-3-Methyl-5-nitroso-2,4-pyriMidinedione
• 1,3-DIETHYL-6-AMINOURACIL