Dimethylformamide → 2-(4-(Trifluoromethoxy)phenyl)pyrimidine-5-carboxaldehyde

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Reaction Steps

n-BuLi (2.5 M, 1.88 mL, 4.7 mmol) was added to a solution of bromide 89 (1.252 g, 3.92 mmol) in THF (40 mL) at −95° C. The solution was stirred for 30 s and then DMF (5 mL) was added. The reaction was stirred at −90° C. for 20 min and then quenched with aqueous NH4Cl. The resulting mixture was partitioned between EtOAc and water, and then column chromatography of the organic portion on silica gel (eluting with 1:7 EtOAc/hexanes) gave 2-[4-(trifluoromethoxy)phenyl]-5-pyrimidinecarbaldehyde (90) (0.778 g, 74%) as a white solid: mp 114-115° C.; 1H NMR (CDCl3) δ 10.16 (s, 1H), 9.22 (s, 2H), 8.62 (d, J=9.0 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H). APCI MS m/z 269 [M+H]+, 301 [M+H+MeOH]+.

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