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

温度

-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) dropwise 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 ppm 2.62 (3H, s), 3.83 (3H, s), 5.29 (1H, s), 5.76 (1H, s), 6.94 (1H, s), 7.38-7.50 (3H, m), 8.00-8.02 (2H, 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レコード

ord-eed124028d824e18af465c1e9bcf4fd5

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08633200B2