反应详情

To a solution of 2-(2,6-diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester (3.3 g, 0.01 mol) at 0° C. in dry THF (50 mL) under nitrogen with magnetic stirring is added n-propyl magnesium chloride (26 mL, 2.0 M, 0.05 mol) in dropwise fashion. The reaction mixture is allowed to warm to room temperature and stirred for 2 h. The reaction mixture is quenched with a saturated aqueous NH4Cl solution (20 mL) and extracted with DCM (100 mL). The DCM layer is dried over sodium sulfate, filtered and evaporated to obtain a residue. Purification by chromatography over silica gel eluting with 10% EtOAc-hexanes affords the title compound as a colorless oil and 1-[2-(2,6-diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]butan-1-ol as a colorless oil. Title compound 1H NMR (300 MHz, CDCl3): δ 7.23-7.29 (m, 1H), 7.13 (d, J=9 Hz, 2H), 3.95 (s, 3H), 2.72 (s, 3H), 2.41 (q, J=7.5 Hz, 4H), 2.18-2.30 (m, 2H), 1.66-1.81 (m, 2H), 1.42-1.54 (m, 2H), 1.05-1.18 (m, 8H), 0.91 (t, J=7.2 Hz, 6H); LC-MS found 371 (MH+). 1-[2-(2,6-Diethylphenyl)-4-methoxy-6-methylpyrimidin-5-yl]butan-1-ol NMR (300 MHz, CDCl3): δ 7.23-7.28 (m, 1H), 7.1 (d, J=9 Hz, 2H), 4.81-5.11 (m, 1H), 4.01(s, 3H), 2.45 (s, 3H), 2.55 (q, J=7.5 Hz, 4H), 1.88-2.00 (m, 1H), 1.30-1.81 (m, 4H), 1.10 (q, J=7.8, 4.8 Hz, 6H), 0.91 (t, J=7.2 Hz, 6H); LC-MS found 328 (MH+).

1. customThe reaction mixture is quenched with a saturated aqueous NH4Cl solution (20 mL)
2. extractionextracted with DCM (100 mL)
3. dry with materialThe DCM layer is dried over sodium sulfate
4. filtrationfiltered
5. customevaporated
6. customto obtain a residue
7. customPurification by chromatography over silica gel eluting with 10% EtOAc-hexanes