2-pyrimidin-2-ylpropan-2-ol synthesis
- Product Name:2-pyrimidin-2-ylpropan-2-ol
- CAS Number:1351763-57-9
- Molecular formula:C7H10N2O
- Molecular Weight:138.1671
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Yield:1351763-57-9 75%
Reaction Conditions:
Stage #1: pyrimidine-2-carboxylic acid methyl ester;methylmagnesium bromide in tetrahydrofuran;diethyl ether at 0 - 20; for 2.5 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;diethyl ether;water;
Steps:
2-(pyrimidin-2-yl)propan-2-ol (27)To a solution of methyl pyrimidine-2-carboxylate (2g, 14.5mmol) in THF (30ml) at 0°C was slowly added a solution of methylmagnesium bromide (3M in Et20, 14.3ml, 43.2mmol). The reaction mixture was stirred 30 min at 0°C then warmed up to room temperature and stirred for 2h before quenching with 2M HCl. The organic materials were then extracted into DCM, washed with brine, dried and concentrated. The crude material was purified by column chromatography (S1O2; DCM:EtOH 1 :0→9.5:0.5) to afford the title compound as a colourless oil (1.48 g, 75%).NMR (CDCI3) δ 8.77 (2H, d, J 5), 7.24 (1H, dd, J 5, 4.75), 4.77 (1H, bs), 1.63 (6H, s).MS (m/e) 139 [M+H]+, Rt 0.36min (QC Method 1)
References:
WO2011/151651,2011,A1 Location in patent:Page/Page column 76