반응 #70168

반응 방정식

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

수율 84.0%

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

수율 84.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도The reaction mixture was then cooled to −78° C.
3. 3
   온도The solution was warmed to room temperature
4. 4
   workup.STIRRINGstirred 5 h
5. 5
   기타The reaction was quenched by the addition of water
6. 6
   기타The organic layer was separated
7. 7
   추출the aqueous layer was extracted with CH2Cl2
8. 8
   세척The combined organics were washed with saturated aqueous Na2S2O3
9. 9
   건조dried over Na2SO4
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo

실험 절차

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).

출처