Reaction #355767

Reaction equation

sodium hydrogen carbonate

bromine

4(1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

→

title compound

Yield 24.0%

4-(4Bromo-1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxvethyl)sulphamoyl]anilino}pyrimidine

Yield 24.0%

Solvents

water

acetic acid

acetic acid

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   ExtractionThe aqueous solution was extracted with EtOAc
3. 3
   Otherdried
4. 4
   Otherthe volatiles removed by evaporation
5. 5
   OtherThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10)

Procedure

A 1M solution of bromine in acetic acid (8.49 ml, 8.49 mmol) was added to a solution of 4(1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Example 35 in WO 02/20512; 3.1g, 7.71mmol) in acetic acid (24 ml) heated at 70° C. under nitrogen. The mixture was stirred at 70° C. for 1 hour, allowed to cool, diluted with water and carefully neutralised with saturated aqueous sodium hydrogen carbonate solution. The aqueous solution was extracted with EtOAc, the extracts combined, dried and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10) to give the title compound (1 g, 24%). NMR: 2.38 (s, 3H), 2.87 (s, 2H), 2.51 (q, 2H), 3.16 (s, 3H), 3.52 (s, 3H), 7.49 (s, 1H), 7.70 (d, 2H), 7.88 (d, 2H), 8.82 (s, 1H).

Source