6-Chloro-3-methyluracil Chemical Properties

Melting point:

278-280°C (dec.)

Density 

0,896 gr/cm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

7.16±0.40(Predicted)

color 

White to Almost white

BRN 

511456

InChI

InChI=1S/C5H5ClN2O2/c1-8-4(9)2-3(6)7-5(8)10/h2H,1H3,(H,7,10)

InChIKey

SGLXGFAZAARYJY-UHFFFAOYSA-N

SMILES

C1(=O)NC(Cl)=CC(=O)N1C

CAS DataBase Reference

4318-56-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 1992

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29335990

6-Chloro-3-methyluracil Usage And Synthesis

Chemical Properties

White solid

Uses

6-Chloro-3-methyluracil have been used in the synthesis of antibacterial agents as inhibitors of Helicobacter pylori glutamate racemase.

Definition

ChEBI: 6-Chloro-3-methyluracil is a member of pyrimidines and an organohalogen compound.

Synthesis

General procedure for the synthesis of 3-methyl-6-chlorouracil from 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione: Water (2.7 mL) was added slowly and dropwise at 0 °C to a 1-methylpyrimidine-2,4,6(1H,3H,5H)-trione (14.2 g, 100 mmol) formed with phosphorus oxychloride (POCl3, 95 mL) in a in a suspension. Subsequently, the reaction mixture was warmed to 80 °C and maintained for 5 hours. Upon completion of the reaction, the resulting brown solution was cooled and the POCl3 was evaporated under reduced pressure.The residue was treated with methanol (MeOH) and the resulting solid was purified by recrystallization from ethanol to give 11.5 g of 3-methyl-6-chlorouracil (yield: 71.6%). The melting point of the product was 279-282 °C (decomposition), which is consistent with literature values (280-282 °C).1H NMR (400 MHz, DMSO-d6) δ 3.10 (s, 3H), 5.90 (s, 1H), 12.4 (br s, 1H).

References

[1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 3, p. 594 - 597
[2] Tetrahedron Asymmetry, 1997, vol. 8, # 14, p. 2319 - 2323
[3] Patent: WO2009/73210, 2009, A1. Location in patent: Page/Page column 76
[4] Patent: WO2006/133261, 2006, A2. Location in patent: Page/Page column 30
[5] Patent: WO2007/143705, 2007, A2. Location in patent: Page/Page column 23

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