Sodium Methoxide → 2-Chloro-5-[(5-isopropyl-2-methylphenoxy)methyl]-4-methoxy-6-methylpyrimidine

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A solution of ˜70% 2,4-dichloro-5-(5-isopropyl-2-methyl-phenoxymethyl)-6-methyl-pyrimidine (2.64 g, ˜5.68 mmol) is cooled to −5° C. under nitrogen with magnetic stirring. A 0.5 M solution of NaOMe in MeOH (11.4 mL) is added in rapid dropwise fashion. After 1 h, reaction is complete based on LC/MS analysis. The reaction mixture is evaporated at reduced pressure, diluted with DCM (15 mL), filtered and evaporated to obtain a pale yellow oil consisting of an isomeric mixture of mono-methoxy adducts. Purification on silica gel (10-60% EtOAc/Hexanes) provides a colorless oil containing the desired isomer (first to elute) plus impurity from the starting material. 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=8 Hz, 1H), 6.82 (s, 1H), 6.78 (d, J=8 Hz, 1H), 5.05 (s, 2H), 4.04 (s, 3H), 2.80 (m, 1H), 2.55 (s, 3H), 2.13 (s, 3H), 1.26 (d, J=6.8 Hz, 6H); LC-MS found 321.1 (MH+), rt=1.73 min, Method 2.

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