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ChemicalBook CAS DataBase List 2-Chloro-5-(phenylmethoxy)-pyrimidine
138274-14-3

2-Chloro-5-(phenylmethoxy)-pyrimidine synthesis

2synthesis methods
-

Yield: 92%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 15; for 8 h;Inert atmosphere;

Steps:

1 Step 1: 5-(Benzyloxy)-2-chloropyrimidine
To a mixture of 2-chloropyrimidin-5-ol (45 g, 345 mmol) in DMF (1 L) was added Cs2CO3(337 g, 1034 mmol) and (bromomethyl)benzene (49.1 mL, 414 mmol). The mixture was stirred at 15 °C for 8 h under N2 atmosphere. Then the mixture was concentrated and saturated aqueous NaHCO3solution (150 mL) was added. The aqueous layer was extracted with EtOAc (500 mL x 2), and the combined extracts were washed with brine (150 mL x 2), dried over Na2SO4, filtered and concentrated to yield a yellow oil of 5-(benzyloxy)-2-chloropyrimidine (78 g, 318 mmol, 92.0% yield):1H NMR (400 MHz, CD3OD) δ ppm 8.45 (s, 2H), 7.52-7.29 (m, 5H), 5.23 (s, 2H); ES-LCMS m/z 221.2, 223.1 [M+H]+.

References:

BP ASSET V, INC. WO2021/97009, 2021, A1 Location in patent:Paragraph 00172

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