Lithium diisopropylamide → HCID 70984495, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing THF (5 mL) was cooled to −78° C. LDA (1.8 M in THF/heptane/ethylbenzene, 3.3 mL, 5.95 mmol) was added followed by a solution of N-[3-methyl-5-(1,3-thiazol-5-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (0.50 g, 1.49 mmol) in THF (5 mL) in one portion and the resulting solution was allowed to stir at −78° C. for thirty minutes. A solution of methyl 4-formylcyclohexanecarboxylate (336 mg, 1.93 mmol) in THF (5 mL) was then added in one portion and the resulting solution was stirred for 1 hour at −78° C. The reaction was then diluted with water and allowed to warm to room temperature. The mixture was then further diluted with water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford methyl 4-{hydroxyl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methyl}cyclohexanecarboxylate as a mixture of 4 isomers. MS ESI calc'd. for C24H25F3N4O3S [M+H]+ 507. found 507. 1H NMR (500 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.82 (d, J=5.1, 1H), 7.96 (s, 1H), 7.95 (s, 1H), 7.44 (s, 1H), 7.27 (d, J=4.9, 1H), 7.15 (s, 1H), 6.20 (d, J=5.0, 1H), 3.55 (s, 3H), 2.30 (s, 3H), 1.99 (m, 1H), 1.88 (m, 2H), 1.66 (s, 3H), 1.45 (m, 1H), 1.37-1.15 (m, 3H).

Provenance & Evidence