تفاعل #355767

معادلة التفاعل

sodium hydrogen carbonate

bromine

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

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title compound

المردود 24.0%

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

المردود 24.0%

المذيبات

water

acetic acid

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool
2. 2
   استخلاصThe aqueous solution was extracted with EtOAc
3. 3
   أخرىdried
4. 4
   أخرىthe volatiles removed by evaporation
5. 5
   أخرىThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10)

الإجراء التجريبي

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).

المصدر