Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:17]1[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]1.C(N(CC)CC)C>C(O)C>[C:11]1([C:10]2[C:3]3[C:2]([N:17]4[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=14-Chloro-5-phenylthieno[2,3-d]pyrimidine (1.5 g, 6.1 mmol), piperidine-4-carboxylic acid (0.86 g, 6.7 mmol) and triethylamine (2.6 mL, 18 mmol) were suspended in dry ethanol (15 mL). The reaction was heated at 140° C. in a microwave for 10 min. The reaction was partitioned between water and DCM. The product was purified by column chromatography using a gradient of 10% methanol in DCM to 100% methanol to give the target compound as an off-white solid (yield=2.1 g). LCMS [M+H]+=440; RT=4.04 min.
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