Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([NH2:22])[CH3:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C=O)C>[I:11][C:10]1[C:3]2[C:2]([NH:22][CH:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[CH3:21])=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1A mixture of 4-chloro-5-iodothieno[2,3-d]pyrimidine (100 mg, 0.34 mmol) and 1-(4-methoxyphenyl)ethylamine (69 mg, 0.37 mmol) and triethylamine (87 μL, 0.9 mmol) in DMF (2.0 mL) was allowed to react for 15 hours at 25° C., then 3 hours at 50° C. The reaction mixture was filtered through a cotton plug and purified by HPLC (Gilson system; Phenomenex column: Luna 5μ C18(2), 150×21.20 mm, 5μ micro) with water/acetonitrile gradient. Appropriate fractions were pooled to provide 70 mg of tan solid.
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