반응 #2204925

반응 방정식

Chlorosulphonic acid

2-anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine

cyclobutylamine

diethylmethylamine

→

title compound

수율 65.6%

4-(1-Methyl-2-isopropylimidazol-5-yl)-2-{4-[N-(cyclobutyl)sulphamoyl]anilino}pyrimidine

수율 65.6%

용매

thionyl chloride

MeOH

반응 조건

후처리

1. 1
   온도then heated at 90° C. for 90 minutes
2. 2
   기타The volatiles were removed by evaporation
3. 3
   기타the residue was dried under high vacuum (<2 mmHg) for 1 hour
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   기타the volatiles were evaporated in vacuo
6. 6
   기타Trituration with water results in a solid which
7. 7
   세척was washed water (3×20 ml)
8. 8
   여과collected by filtration
9. 9
   기타dried under vacuum at 60° C.

실험 절차

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1-methyl-2-isopropylimidazol-5-yl)pyrimidine (Method 71; 158 mg, 0.54 mmol) in thionyl chloride (3 ml) cooled at 0° C. and the mixture stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of cyclobutylamine (100 μl, 1.08 mmol) and diethylmethylamine (1 ml, 15 mmol) in MeOH (3 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Trituration with water results in a solid which was washed water (3×20 ml) collected by filtration and dried under vacuum at 60° C. to yield the title compound (151 mg, 65%) as a solid. NMR: 1.24 (d, 6H), 1.45 (m, 2H), 1.70 (m, 2H), 1.90 (m, 2H), 3.17 (m, 1H), 3.58 (m, 1H), 3.98 (s, 3H), 7.19 (d, 1H), 7.70 (m, 4H), 7.92 (d, 2H), 8.41 (d, 1H), 9.90 (brs, 1H); m/z 427.

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