Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate → (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

To a solution of ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate (30 g, 132 mmol) in THF (300 mL) was added LiAlH4 (7.5 g, 198 mmol). The reaction mixture was stirred for 1 h at RT. The reaction was carefully quenched with 10 mL water, 7 mL of 10% aq NaOH. The mixture was stirred for 1 h, filtered and the filtrate was concentrated to give (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (22.0 g, 90% yield). 1H NMR (300 MHz, DMSO-d6): 7.79 (s, 1 H), 6.79 (m, 1 H), 5.04 (t, J=5.4 Hz, 1 H), 4.27 (d, J=5.4 Hz, 2H), 2.83 (d, J=4.8 Hz, 3 H), 2.40 (s, 3 H). MS (ESI) m/z: 186.1 (M+H+).

1. customThe reaction was carefully quenched with 10 mL water, 7 mL of 10% aq NaOH
2. stirringThe mixture was stirred for 1 h
3. filtrationfiltered
4. concentrationthe filtrate was concentrated

ORDレコード

ord-e94ccc15e0fb4ab2b314205efbf8ec01

出典データセット

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07897762B2