Sodium Hydroxide → (E)-3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)prop-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

A hexane solution of diisobutylaluminum hydride (1 mL of a 1.0M solution, 1.0 mmol, 4.0 equiv.) was added to a cooled (−78° C.) solution of (E)-methyl 3-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)acrylate (100 mg, 0.248 mmol, 1.0 equiv.) in THF (2 mL). After stirring for 1 h at −78° C., additional disobutylalumium hydride solution (0.25 mL of a 1.0M solution, 0.25 mmol, 1.0 equiv.) was added. After another 30 min, NaOH solution (1N) was added and the reaction mixture was allowed to warm slowly to room temperature for 10 min. The organic layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organic layers were washed with water, brine, dried (Na2SO4) and filtered. The filtrate was concentrated to afford crude. The crude was crystallized with ethanol to afford compound (E)-3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)prop-2-en-1-ol (Compound 53) (80 mg, 96%). LC-MS (m/z): 334.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 0.71-0.72 (m, 2H), 0.96-0.98 (m, 2H), 1.91-1.98 (m, 1H), 4.15 (t, J=5.2 Hz, 2H), 4.87 (m, 1H), 6.34 (dt, J1=4.8 Hz, J2=15.6 Hz, 1H), 6.48 (s, 1H), 6.80 (d, J=16 Hz, 1H), 7.48-7.51 (m, 3H), 8.28-8.30 (m, 2H), 8.47 (s, 1H), 9.05 (s, 1H), 12.15 (s, 1H).

Provenance & Evidence