تفاعل #610445

معادلة التفاعل

N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(thiazol-2-yl)acetamide

CDI

→

6-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione

المردود 34.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooled mixture was partitioned between EtOAc and water
2. 2
   غسيلThe organic layer was washed with brine
3. 3
   استخلاصthe combined aqueous layers were extracted with EtOAc
4. 4
   أخرىThe combined organic layers were dried
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by column chromatography on silica gel (40 g)
7. 7
   غسيلeluting with 70% EtOAc-hexanes

الإجراء التجريبي

A mixture of N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(thiazol-2-yl)acetamide (0.45 g, 1.26 mmol) and CDI (0.815 g, 5.02 mmol) in toluene (6.5 mL) was heated at 110° C. for 2 h. The cooled mixture was partitioned between EtOAc and water. The organic layer was washed with brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried and concentrated. The residue was purified by column chromatography on silica gel (40 g), eluting with 70% EtOAc-hexanes, to give slightly impure 6-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione as a tan solid (34% yield). The material was used without further purification. Mass spectrum m/z 385 (M+H)+.

المصدر