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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (S)-4-methyloxazolidin-2-one (9.0 mg, 0.089 mmol) in dry DMF (0.5 mL) was cooled to 0° C. Sodium hexamethyldisilazide (0.089 mL, 0.089 mmol) was added and the resulting yellow solution stirred for 10 minutes before addition of a solution of 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl 4-methylbenzenesulfonate (20.0 mg, 0.0356 mmol) in DMF (0.5 mL). The mixture was then brought to ambient temperature prior to heating at 80° C. for 1 hour. The cooled reaction mixture was poured into saturated aqueous NH4Cl and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 1-2% MeOH/dichloromethane afforded the protected intermediate which was taken up in dichloromethane (1 mL). Trifluoroacetic acid (3 mL) was added and the mixture stirred at ambient temperature for 12 hours. The reaction mixture was concentrated, washed with saturated aqueous NaHCO3, extracted into ethyl acetate, dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 2-4% MeOH/dichloromethane, afforded (S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-methyloxazolidin-2-one as a light yellow solid (1 mg, 8%). LCMS (APCI+) m/z 361 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.82 (d, J=7.8 Hz, 1H), 8.54 (s, 1H), 8.17 (d, J=8.6 Hz, 2H), 7.97 (d, J=7.8 Hz, 1H), 7.91 (d, J=8.6 Hz, 2H), 7.14 (s, 2H), 5.06-5.13 (m, 1H), 4.65 (t, J=8.2 Hz, 1H), 4.21-4.24 (m, 1H), 1.66 (d, J=6.2 Hz, 3H). was then brought to ambient temperature The cooled reaction mixture extracted with EtOAc The combined organic extracts were dried over sodium sulfate filtered concentrated Purification of the crude material by column chromatography eluting with 1-2% MeOH/dichloromethane afforded the protected intermediate which The reaction mixture was concentrated washed with saturated aqueous NaHCO3 extracted into ethyl acetate dried over sodium sulfate filtered concentrated Purification of the crude material by column chromatography eluting with 2-4% MeOH/dichloromethane

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

Procedure: Using methyl 4-bromomethylbenzoate (500 mg) and (S)-4-methyloxazolidin-2-one (243 mg) and by the reaction and treatment in the same manner as in Preparation Example 42, the title compound (440 mg) was obtained. by the reaction and treatment in the same manner as in Preparation Example 42

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (S)-4-methyloxazolidin-2-one (9.0 mg, 0.089 mmol) in dry DMF (0.5 mL) was cooled to 0° C. Sodium hexamethyldisilazide (0.089 mL, 0.089 mmol) was added and the resulting yellow solution stirred for 10 minutes before addition of a solution of 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl 4-methylbenzenesulfonate (20.0 mg, 0.0356 mmol) in DMF (0.5 mL). The mixture was then brought to ambient temperature prior to heating at 80° C. for 1 hour. The cooled reaction mixture was poured into saturated aqueous NH4Cl and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 1-2% MeOH/dichloromethane afforded the protected intermediate which was taken up in dichloromethane (1 mL). Trifluoroacetic acid (3 mL) was added and the mixture stirred at ambient temperature for 12 hours. The reaction mixture was concentrated, washed with saturated aqueous NaHCO3, extracted into ethyl acetate, dried over sodium sulfate, filtered and concentrated. Purification of the crude material by column chromatography, eluting with 2-4% MeOH/dichloromethane, afforded (S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-methyloxazolidin-2-one as a light yellow solid (1 mg, 8%). LCMS (APCI+) m/z 361 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.82 (d, J=7.8 Hz, 1H), 8.54 (s, 1H), 8.17 (d, J=8.6 Hz, 2H), 7.97 (d, J=7.8 Hz, 1H), 7.91 (d, J=8.6 Hz, 2H), 7.14 (s, 2H), 5.06-5.13 (m, 1H), 4.65 (t, J=8.2 Hz, 1H), 4.21-4.24 (m, 1H), 1.66 (d, J=6.2 Hz, 3H). was then brought to ambient temperature The cooled reaction mixture extracted with EtOAc The combined organic extracts were dried over sodium sulfate filtered concentrated Purification of the crude material by column chromatography eluting with 1-2% MeOH/dichloromethane afforded the protected intermediate which The reaction mixture was concentrated washed with saturated aqueous NaHCO3 extracted into ethyl acetate dried over sodium sulfate filtered concentrated Purification of the crude material by column chromatography eluting with 2-4% MeOH/dichloromethane