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ChemicalBook CAS DataBase List 2-Pyrimidinemethanol
42839-09-8

2-Pyrimidinemethanol synthesis

4synthesis methods
2-PYRIMIDINECARBOXYLIC ACID, METHYL ESTER

34253-03-7

2-Pyrimidinemethanol

42839-09-8

Synthesis of pyrimidin-2-ylmethanol (12): ester 11 (0.43 g, 3.09 mmol) was dissolved in EtOH (30 mL), stirred and cooled to 0 °C. NaBH4 (0.114 g, 3.09 mmol) was slowly added under stirring and the reaction mixture continued to stir for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of the raw materials, the reaction was quenched with cold water. Subsequently, the reaction mixture was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with MeOH/CH2Cl2 (1:49) as eluent to afford alcohol 12 (0.145 g, 37% yield). The product had an Rf value of 0.3 in 10% MeOH/CHCl3.1H NMR (500 MHz, CDCl3) δ: 8.75 (d, J = 5.5 Hz, 2H), 7.26-7.22 (m, 1H), 4.85 (s, 2H). Mass spectrum (ESI): m/z 111.1 [M+H]+.

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: hydrogenchloride / 16 h / 0 °C
2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / Inert atmosphere

References:

ENVIVO PHARMACEUTICALS, INC.;RIPKA, Amy;SHAPIRO, Gideon;MCRINER, Andrew WO2012/40230, 2012, A1

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