تفاعل #60626

معادلة التفاعل

Chlorosulphonic acid

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

2-Anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

2-methoxyethylamine

diethylmethylamine

→

title compound

المردود 24.4%

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

المردود 24.4%

المذيبات

thionyl chloride

MeOH

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
   أخرىThe residue was purified by chromatography
7. 7
   غسيلeluting with DCM/MeOH (98:2)

الإجراء التجريبي

Chlorosulphonic acid (70 μl, 1.0 mmol) was added dropwise to solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 75 mg, 0.24 mmol) in thionyl chloride (2 ml) cooled at 0° C. and the mixture was 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 (100 μl, 0.5 mmol) and diethylmethylamine (0.5 ml, 7.5 mmol) in MeOH (1.5 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. The residue was purified by chromatography eluting with DCM/MeOH (98:2) to give the title compound (26 mg, 24%) as glassy solid. NMR: 1.53 (d, 6H) 2.86 (q, 2H) 3.17 (s, 3H) 3.28 (t, 2H) 5.65 (m, H) 7.3 (t, 1H) 7.50 (t, 1H) 7.71 (d, 2H) 7.83 (s, 1H) 7.89 (d, 2H) 8.68 (d, 1H) 9.81 (s, 1H) 10.11 (s, 1H).

المصدر