反応 #1614157

反応方程式

(R)-5-bromo-2-chloro-N-(1-phenylethyl)pyrimidin-4-amine

methyl but-2-ynoate

lithium chloride

potassium carbonate

→

(R)-methyl 2-chloro-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

収率 15.2%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONback-filled with nitrogen for three times
2. 2
   ろ過The reaction mixture was filtered
3. 3
   濃縮the filtrate was concentrated in vacuo
4. 4
   抽出extracted with ethyl acetate (50 mL)
5. 5
   洗浄washed with water (50 mL)
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   その他purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

実験手順

A solution of (R)-5-bromo-2-chloro-N-(1-phenylethyl)pyrimidin-4-amine (5 g, 16 mmol), methyl but-2-ynoate (3.1 g, 32 mmol), lithium chloride (690 mg, 16 mmol), potassium carbonate (5.5 g, 40 mmol) and palladium acetate (360 mg, 1.6 mmol) in N,N-dimethylformamide (50 mL) was degassed and back-filled with nitrogen for three times, then heated at 120° C. for 4 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo, extracted with ethyl acetate (50 mL), washed with water (50 mL), dried over anhydrous magnesium sulfate and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give (R)-methyl 2-chloro-6-methyl-7-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a yellow oil (800 mg, 15%). LRMS (M+H+) m/z: calcd 329.09. found 329. 1H NMR (300 MHz, CDCl3): δ 9.16 (s, 1H), 7.39-7.18 (m, 5H), 6.45-6.42 (m, 1H), 3.96 (s, 3H), 2.57 (s, 3H), 2.05 (d, J=7.2 Hz, 3H).

出典