反应 #60882

反应方程式

iodine

Butyllithium

diisopropylamine

NH4Cl

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

→

title compound

收率 77.0%

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

收率 77.0%

溶剂

THF

THF

water

THF

反应条件

后处理

1. 1
   其他recooled to −78° C.
2. 2
   其他A purple solution resulted
3. 3
   workup.STIRRINGstirring at −78° C.
4. 4
   workup.WAITcontinued for 1 hours
5. 5
   温度before warming to ambient temperature
6. 6
   workup.STIRRINGstirring for a further 1.5 hr
7. 7
   萃取the reaction mixture extracted with DCM (500 mL)
8. 8
   洗涤the organic layer was washed with Na2S2O3 (2M, aq) (2×50 mL), water (2×200 mL)
9. 9
   干燥dried (MgSO4)
10. 10
    过滤filtered
11. 11
    浓缩concentrated in vacuo
12. 12
    其他The crude product was triturated with DCM (50 mL)

实验过程

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%);

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