반응 #60882

반응 방정식

iodine

Butyllithium

diisopropylamine

NH4Cl

4-(methylthio)thieno[2,3-d]pyrimidine

→

title compound

수율 77.0%

4-Methylthio-6-iodo-thieno[2,3-d]pyrimidine

수율 77.0%

용매

THF

THF

water

THF

반응 조건

후처리

1. 1
   기타recooled to −78° C.
2. 2
   기타A purple solution resulted
3. 3
   workup.STIRRINGstirring at −78° C.
4. 4
   workup.WAITcontinued for 1 hours
5. 5
   온도before warming to ambient temperature
6. 6
   workup.STIRRINGstirring for a further 1.5 hr
7. 7
   추출the reaction mixture extracted with DCM (500 mL)
8. 8
   세척the organic layer was washed with Na2S2O3 (2M, aq) (2×50 mL), water (2×200 mL)
9. 9
   건조dried (MgSO4)
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo
12. 12
    기타The crude product was triturated with DCM (50 mL)

실험 절차

Butyllithium (1.6 M in hexane, 32.8 mL) was added dropwise to a stirred solution of diisopropylamine (7.36 mL) in THF (170 mL) at −78° C. under an inert atmosphere. The reaction mixture was warmed to 0° C., stirred for 20 min, recooled to −78° C. and 4-(methylthio)thieno[2,3-d]pyrimidine (J. Heterocycl. Chem. 1975, 12, 921-924) (9.11 g) in THF (17 mL) added. A purple solution resulted and then iodine (19.0 g) in THF (20 mL) was added and stirring at −78° C. continued for 1 hours before warming to ambient temperature and stirring for a further 1.5 hr. Saturated aqueous NH4Cl (3 mL), then water (500 mL) were added and the reaction mixture extracted with DCM (500 mL), the organic layer was washed with Na2S2O3 (2M, aq) (2×50 mL), water (2×200 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was triturated with DCM (50 mL) to afford the title compound as a brown solid (11.8 g, 77%);

출처