Iodine → 4-Chloro-6-iodothieno(3,2-d)pyrimidine
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[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[C:11]2[S:18][CH:17]=[CH:16][C:12]=2[N:13]=[CH:14][N:15]=1.[I:19]I.O>C1COCC1>[Cl:9][C:10]1[C:11]2[S:18][C:17]([I:19])=[CH:16][C:12]=2[N:13]=[CH:14][N:15]=1[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[C:11]2[S:18][CH:17]=[CH:16][C:12]=2[N:13]=[CH:14][N:15]=1.[I:19]I.O>C1COCC1>[Cl:9][C:10]1[C:11]2[S:18][C:17]([I:19])=[CH:16][C:12]=2[N:13]=[CH:14][N:15]=1To a solution of LDA (1.8M, 20.6 mL, 37.1 mmol) in THF (65 mL) at −78° C. was added 4-chloro-thieno[3,2-d]pyrimidine (5.26 g, 31 mmol) in THF (50 mL) dropwise over 1 hour. After stirring for 20 minutes, I2 (12.7 g, 50 mmol) in THF (40 mL) was added to the mixture at −78° C. dropwise. The mixture was stirred at the same temperature for 20 minutes and then warmed up to room temperature for 2 hours. The mixture was poured into water (100 mL) and stirred for 30 minutes. The solid was filtered and washed with water and Hexane-Hexanes/DCM (50:1) to afford the product 4-Chloro-6-iodothieno[3,2-d]pyrimidine (6.86 g, 75%). 1H NMR (DMSO, 400 Hz) δ 8.97 (s, 1H), 8.15 (s, 1H).
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