(4S)-4-propyl-1,3-oxazolidin-2-one

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

Procedure: To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid. the solids were collected by filtration Purification of the crude material by normal phase column chromatography eluting with 1-10% EtOAc/dichloromethane

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

Procedure: To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid. the solids were collected by filtration Purification of the crude material by normal phase column chromatography eluting with 1-10% EtOAc/dichloromethane

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

Procedure: A solution of triphosgene (0.431 g, 1.45 mmol) in THF (5 mL) was added dropwise to a stirred solution of (S)-2-aminopentan-1-ol (0.500 g, 4.85 mmol) and Et3N (1.49 mL, 10.7 mmol) in THF (22 mL) at 0° C. under N2. The reaction mixture was stirred at ambient temperature for 2 hours. After cooling, the suspension was filtered through GF/F paper and concentrated in vacuo. The residue was taken up in EtOAc and washed with 10% HCl, dried and concentrated to give (S)-4-propyloxazolidin-2-one (0.348 g, 55%) as a clear oil. After cooling the suspension was filtered through GF/F paper concentrated in vacuo washed with 10% HCl dried concentrated

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

Procedure: To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid. the solids were collected by filtration Purification of the crude material by normal phase column chromatography eluting with 1-10% EtOAc/dichloromethane

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

Procedure: A solution of triphosgene (0.431 g, 1.45 mmol) in THF (5 mL) was added dropwise to a stirred solution of (S)-2-aminopentan-1-ol (0.500 g, 4.85 mmol) and Et3N (1.49 mL, 10.7 mmol) in THF (22 mL) at 0° C. under N2. The reaction mixture was stirred at ambient temperature for 2 hours. After cooling, the suspension was filtered through GF/F paper and concentrated in vacuo. The residue was taken up in EtOAc and washed with 10% HCl, dried and concentrated to give (S)-4-propyloxazolidin-2-one (0.348 g, 55%) as a clear oil. After cooling the suspension was filtered through GF/F paper concentrated in vacuo washed with 10% HCl dried concentrated