2-(Benzenesulfonyl)-3-phenyloxaziridine → Methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

Temperature

-78 °C

To a stirred solution of KHMDS (0.5 M in toluene, 9.50 mL, 4.75 mmol) in THF (24 mL) at −78° C. was added a solution of methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1 g, 3.17 mmol) in THF (24 mL) drop wise over 40 min. The mixture was stirred at −78° C. for 30 min. A solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (1.241 g, 4.75 mmol) in THF (24 mL) was added over 20 min and the reaction mixture was stirred for additional 30 min at −78° C. The reaction mixture was quenched with saturated NH4Cl aqueous solution (4 mL). The reaction mixture was allowed to warm to room temperature and then diluted with ethyl acetate (100 mL). The organic phase was washed with water and brine and dried with sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (535 mg, 50.9%). 1H-NMR (500 MHz, CDCl3) δ 2.62 (3 H, s), 3.83 (3 H, s), 5.29 (1 H, s), 5.76 (1 H, s), 6.94 (1 H, s), 7.38-7.50 (3 H, m), 8.00-8.02 (2 H, m).

1. stirringthe reaction mixture was stirred for additional 30 min at −78° C
2. customThe reaction mixture was quenched with saturated NH4Cl aqueous solution (4 mL)
3. temperatureto warm to room temperature
4. additiondiluted with ethyl acetate (100 mL)
5. washThe organic phase was washed with water and brine
6. dry with materialdried with sodium sulfate
7. customThe solvent was evaporated
8. customPurification by silica gel chromatography

ORD record

ord-89a32f0499b24ab0981bbb6ddc2e114c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034882B2