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

温度

-78 °C

To a stirred solution of KHMDS (0.5 M in toluene, 4.6 mL, 4.75 mmol) in THF (12 mL) at −78° C. was added a solution of methyl 2-(7-chloro-5-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.48 g, 1.5 mmol) in THF (12 mL) over 20 mins. The reaction mixture was stirred at −78° C. for 30 min. A solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (0.6 g, 2.3 mmol) in THF (12 mL) was added over 10 min and the resulted reaction mixture was stirred for an additional 30 min at −78° C. The reaction mixture was quenched with saturated NH4Cl aqueous solution (2 mL). The mixture was allowed to warm up to room temperature and diluted with EtOAc (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 (250 mg, 51%). 1H-NMR (500 MHz, DMSO-d6) δ ppm 2.65 (3H, s), 3.7 (3H, s), 5.79 (1H, s), 6.62 (1H, s), 7.35-7.59 (3H, m), 8.95 (1H, s).

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

ORDレコード

ord-db227adfd0f04560a01c31e47b0008b7

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08633200B2