2-hydroxy-1-piperazin-1-ylpropan-1-one

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

Procedure: In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min). stirred at room temperature for 3 hours washed with water, brine dried over anhydrous sodium sulfate evaporated under reduced pressure to provide the crude product The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

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

Procedure: In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min). stirred at room temperature for 3 hours washed with water, brine dried over anhydrous sodium sulfate evaporated under reduced pressure to provide the crude product The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

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

Procedure: In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min). stirred at room temperature for 3 hours washed with water, brine dried over anhydrous sodium sulfate evaporated under reduced pressure to provide the crude product The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)