Acetic Acid → HCID 11785433, compound

Participants

Reaction Conditions

Reaction Steps

The above amino alcohol HCl salt (1.00 g, 4.32 mmol) was suspended in ammonium hydroxide and heated in a stainless steel pressure vessel at 90° C. for 3 h. The solvent was removed in vacuo. The resulting free base was used without further purification. 1-(4-Amino-9-propyl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-7-yl)-piperidin-4-one (Example 4) (570 mg, 1.67 mmol) and the above amide (300 mg, 1.67 mmol) were dissolved in 10 mL of dry DMF. MP-Cyanoborohydride (0534 mg, 1.20 mmol) was added followed by 0.5 mL of glacial acetic acid. This mixture was shaken for 16 h. The resin was removed by filtration and washed with MeOH and dichloromethane. The filtrate was evaporated. The residue was treated with 2 M sodium carbonate solution. The resulting solid was collected by filtration and purified with flash chromatography (110 g SiO2, 10-20% EtOH/CH2Cl2 1% NH4OH, 50 mL/min, 100 minutes, UV detection at 254 nm) to give the title compound as a yellow solid (0.360 g, 49%).

Provenance & Evidence