تفاعل #355766

معادلة التفاعل

2-methoxyethylamine

Chlorosulphonic acid

2-anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine

→

title compound

المردود 40.0%

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

المردود 40.0%

المذيبات

isopropanol

thionyl chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthen heated at 90° C. for 90 minutes
2. 2
   أخرىThe volatiles were removed by evaporation
3. 3
   أخرىthe residue was dried under high vacuum (<2 mmHg) for 1 hour
4. 4
   workup.STIRRINGThe mixture was stirred for 30 minutes
5. 5
   أخرىthe volatiles were evaporated in vacuo
6. 6
   workup.ADDITIONWater (20 ml) was added
7. 7
   استخلاصextracted EtOAc (2×20ml)
8. 8
   أخرىdried
9. 9
   أخرىevaporated in vacuo

الإجراء التجريبي

Chlorosulphonic acid (150 μl, 2.16 mmol) was added dropwise to solution of 2-anilino-4-(1,2-diethylmethylimidazol-5-yl)pyrimidine (Method 13; 28 mg, 0.09 mmol) in thionyl chloride (2 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 2-methoxyethylamine (300 μl, 3.45 mmol) in isopropanol (2 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. Water (20 ml) was added and extracted EtOAc (2×20ml). The organic layers were combined, dried and evaporated in vacuo to give the title compound (16 mg, 40%) as a orange solid. NMR 2.35-2.45 (m, 9H), 2.7 (q, 2H), 2.89 (q, 2H), 3.40-3.28 (m, 2H), 3.60-3.58 (m, 3H), 4.35 (m, 2H), 7.0 (d, 1H), 7.49 (t, 1H), 7.70 (d, 2H), 7.9 (d, 2H), 8.55 (d, 1H); m/z 445.

المصدر