Tetrabutylammonium Fluoride → HCID 58169324, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-((tert-butyldimethylsilyloxy)methyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (50 mg, 0.119 mmol, 1.0 eq) in anhydrous THF (2 mL), TBAF (0.5 mL, 0.5 mmol, 4.2 equiv., 1M in THF) was added dropwise. The reaction mixture was stirred at 20° C. for 2 h and then concentrated to give a residue. The residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 20:1 as eluent) to afford title compound (4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)methanol (Compound 123) (10 mg, 27.4%) as yellowish solid. LC-MS (m/z)=308.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.75 (m, 2H), 0.97-0.99 (m, 2H), 1.96-1.98 (m, 1H), 4.59 (s, 2H), 5.63 (s, 1H), 6.56 (s, 1H), 7.51 (m, 3H), 8.32 (m, 3H), 8.83 (s, 1H), 12.15 (s, 1H).

Provenance & Evidence