(E)-5-(4-(benzyloxy)styryl)-N-(4-(difluoromethoxy)phenyl)pyrimidin-2-amine → 4-(2-(2-((4-(Difluoromethoxy)phenyl)amino)pyrimidin-5-yl)ethyl)phenol
Reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:12](/[CH:13]=[CH:14]/[C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[CH:24][CH:23]=3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[F:31][CH:29]([F:30])[O:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:18]2[N:17]=[CH:16][C:15]([CH2:14][CH2:13][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:33][CH:32]=3)=[CH:20][N:19]=2)=[CH:23][CH:24]=1Participants
Procedure
To a solution of (E)-5-(4-(benzyloxy)styryl)-N-(4-(difluoromethoxy)phenyl)pyrimidin-2-amine (0.04 g, 0.090 mmol) in methanol (5 mL) was added Pd/C (0.03 g, 0.282 mmol) and stirred at room temperature under H2 (1 atom) for 3 h. The reaction mass was filtered through Celite, concentrated and purified by preparative HPLC on a Waters Xbridge C18 column (19×150 mm, 5 μm) using 0-100% mobile phase B (95:5 Acetonitrile:water with 10 mM NH4OAc) in mobile phase A (5:95 Acetonitrile:water with 10 mM NH4OAc) to give 4-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)ethyl)phenol (0.013 g, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.73 (s, 4H), 6.66 (d, J=8.40 Hz, 2H), 6.83-7.35 (m, 5H), 7.71-7.79 (m, 2H), 8.26 (s, 2H), 9.15 (br. s., 1H), 9.55 (s, 1H). LCMS: RT 2.14 min, (M+H)+358.1.
Workup
- filtrationThe reaction mass was filtered through Celite
- concentrationconcentrated
- custompurified by preparative HPLC on a Waters Xbridge C18 column (19×150 mm, 5 μm)
Sources & evidence
- ORD record
- ord-687d57ef32624a98942acc0ad5406472
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841301B2
Reaction notes
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