1-(piperidin-4-ylmethyl)pyrrolidin-2-one;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-Piperidin-4-ylmethyl-pyrrolidin-2-one hydrochloride salt in anhydrous 1,2-dichloroethane was added triethylamine (47 μL), the reaction mixture was stirred at room temperature for 2 hours. 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (99 mg) and glacial acetic acid were added, the reaction mixture was stirred at room temperature for 4 hours. Sodium triacetoxyborohydride (96 mg) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine, dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified using column chromatography to give 2-[1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-ylmethyl]-cyclopentanone (73 mg). the reaction mixture was stirred at room temperature for 4 hours The reaction mixture was stirred at room temperature overnight washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine dried (MgSO4) the solvents removed in vacuo to give a crude residue This was purified

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(2-Oxo-pyrrolidin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester in dichloromethane was added 2M hydrogen chloride in ether (1.78 ml). The reaction mixture was stirred at room temperature for 6 hours. The solvents were removed in vacuo to yield 1-Piperidin-4-ylmethyl-pyrrolidin-2-one hydrochloride salt. The solvents were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-Piperidin-4-ylmethyl-pyrrolidin-2-one hydrochloride salt in anhydrous 1,2-dichloroethane was added triethylamine (47 μL), the reaction mixture was stirred at room temperature for 2 hours. 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (99 mg) and glacial acetic acid were added, the reaction mixture was stirred at room temperature for 4 hours. Sodium triacetoxyborohydride (96 mg) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine, dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified using column chromatography to give 2-[1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-ylmethyl]-cyclopentanone (73 mg). the reaction mixture was stirred at room temperature for 4 hours The reaction mixture was stirred at room temperature overnight washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine dried (MgSO4) the solvents removed in vacuo to give a crude residue This was purified