反応 #84649

反応方程式

2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-aminobicyclo[3.1.0]hexan-3-ylcarbamate

2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline

sodium bicarbonate

→

title compound

収率 62.5%

2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-(6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-ylamino)bicyclo[3.1.0]hexan-3-ylcarbamate

収率 62.5%

溶媒

N-methyl-2-pyrrolidone

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with water (eight times) and brine (50 mL)
2. 2
   乾燥The organic layer was dried over sodium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他to afford a crude product, which
6. 6
   その他was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:2)

実験手順

A solution of 2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-aminobicyclo[3.1.0]hexan-3-ylcarbamate (250 mg, 0.977 mmol), 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (300 mg, 0.814 mmol) and sodium bicarbonate (205 mg, 2.442 mmol) in N-methyl-2-pyrrolidone (10 mL) was stirred at 100° C. overnight. The reaction solution was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with water (eight times) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford a crude product, which was purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:2) to afford the title compound (300 mg, 52%) as a yellow solid. MS (ES+) C28H34Cl2N4O4Si requires: 588, 590, found: 589, 591 [M+H]+.

出典