Diisobutylaluminum hydride → 2-Cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol
Reaction equation
C[O:2][C:3](=O)[CH:4]([CH:20]1[CH2:22][CH2:21]1)[O:5][C:6]1[C:7]([Cl:19])=[N:8][C:9]([Cl:18])=[N:10][C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH:20]1([CH:4]([O:5][C:6]2[C:7]([Cl:19])=[N:8][C:9]([Cl:18])=[N:10][C:11]=2[N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:3][OH:2])[CH2:22][CH2:21]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of cyclopropyl-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid methyl ester (233 mg, 0.64 mmol) in THF (6.5 mL) at −78° C. under an atmosphere of nitrogen was added DIBAL-H (1.93 mL, 1.93 mmol, 1.0M in toluene) dropwise. The reaction mixture was warmed to RT and stirred for 20 hours before being quenched with Rochelle's salt (15 mL, 1M aqueous solution). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic phases were dried (Na2SO4) then concentrated in vacuo to give 2-Cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol as a colorless gum (215 mg, quantitative). 1H NMR (CDCl3): δ 3.94-3.88 (2H, m), 3.87-3.82 (4H, m), 3.79-3.73 (4H, m), 3.48-3.41 (1H, m), 1.11-0.99 (1H, m), 0.60-0.51 (1H, m), 0.51-0.42 (1H, m), 0.19-0.11 (1H, m), 0.03-−0.05 (1H, m).