反应 #70168

反应方程式

n-BuLi

2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

3-amino-4-methyl-thiophene-2-carboxylic acid ethyl ester

I2

→

2-chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-c]pyrimidine

收率 84.0%

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

收率 84.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他prepared
2. 2
   温度The reaction mixture was then cooled to −78° C.
3. 3
   温度The solution was warmed to room temperature
4. 4
   workup.STIRRINGstirred 5 h
5. 5
   其他The reaction was quenched by the addition of water
6. 6
   其他The organic layer was separated
7. 7
   萃取the aqueous layer was extracted with CH2Cl2
8. 8
   洗涤The combined organics were washed with saturated aqueous Na2S2O3
9. 9
   干燥dried over Na2SO4
10. 10
    过滤filtered
11. 11
    浓缩concentrated in vacuo

实验过程

To a solution of 2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidine 39 (3.0 g, 11.1 mmol; prepared according to the procedure for the synthesis of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine but commencing with 3-amino-4-methyl-thiophene-2-carboxylic acid ethyl ester) in THF (60 mL) at −78° C. was added n-BuLi (8.9 mL, 2.5 M in Et2O). The resulting slurry was warmed to −40° C. and stirred 50 min. The reaction mixture was then cooled to −78° C. and a solution of I2 (5.6 g, 22.2 mmol) in THF (30 mL) was added. The solution was warmed to room temperature and stirred 5 h. The reaction was quenched by the addition of water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous Na2S2O3, dried over Na2SO4, filtered, and concentrated in vacuo to provide 2-chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-c]pyrimidine 41 (3.8 g, 84% yield).

来源