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6-Chloro-3-methyluracil

Product Name6-Chloro-3-methyluracil
CAS4318-56-3
MFC5H5ClN2O2
MW160.56
EINECS610-113-2
MOL File4318-56-3.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

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

2565-47-1

4318-56-3

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

6-Chloro-3-methyluracil

Chemical Properties

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Usage And Synthesis

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