Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].[C:19](O)(C)(C)C.CCOC(C)=O>O.Cl>[CH2:14]([N:16]([CH2:17][CH3:18])[C:2]1[C:3]2[C:10]3[CH2:19][CH2:11][CH2:12][CH2:13][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:15]To a slurry of 0.044 g 4-chloro-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine (0.196 mmol) in 1 mL of 100:1 H2O/HCl was added 0.014 g (0.02 mL, 0.106 mmol) diethylamine. The mixture was heated to reflux, and an additional 0.2 mL diethylamine and 1 mL of t-butanol were added and heated continued at reflux for an additional 1 h. TLC (20% EtOAc/80% pet ether) showed complete reaction and the 1H NMR of the isolated material was consistent with the desired product.
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