反応 #359689

反応方程式

4-Cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde

3-Methoxy-propionic acid methyl ester

LiHMDS

→

8-cyclopentyl-6-methoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

収率 24.1%

溶媒

ethyl acetate

water

ethyl acetate

—

hexanes

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas slowly added
2. 2
   温度to reflux for 7 days
3. 3
   その他the layers separated
4. 4
   乾燥the organic layer dried over MgSO4
5. 5
   その他the solvent evaporated
6. 6
   その他to give a crude oil
7. 7
   その他to give a precipitate which
8. 8
   ろ過was collected by filtration

実験手順

3-Methoxy-propionic acid methyl ester (9.95 g, 84.2 mmol) was dissolved in tetrahydrofuran (40 mL) to which LiHMDS (89 mL, 88.9 mmol, 1.0 M in THF) was slowly added. 4-Cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (10.0 g, 42.2 mmol) was then added neat and the reaction mixture brought to reflux for 7 days. The reaction mixture was diluted with ethyl acetate and water, the layers separated, the organic layer dried over MgSO4 and the solvent evaporated to give a crude oil. The crude product was dissolved in ethyl acetate and diluted with hexanes to give a precipitate which was collected by filtration to give 8-cyclopentyl-6-methoxymethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as an off-white solid (3.11 g, 24.1%). 1H NMR 6 (400 MHz, CDCl3) 8.46 (s, 1H), 7.49 (t, J=1.7 Hz, 1H), 5.81 (m, 1H), 4.28 (d, J=1.7 Hz, 1H), 3.37 (s, 3H), 2.47 (s, 3H), 2.18 (m, 2H), 1.93 (m, 2H), 1.73 (m, 2H), 1.55 (m, 2H).

出典