Sodium Hydroxide → {4-[2-Amino-6-(5-chloro-2-methoxy-phenyl)-pyrimidin4-ylamino]-phenyl}-methanol

HRID 28534Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[O:24][CH3:25])[N:14]=[C:13]([NH2:26])[N:12]=2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[NH2:26][C:13]1[N:12]=[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=2)[CH:16]=[C:15]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])[N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the title compound of Example 9 in tetrahydrofuran (5.0 ml), cooled to 0° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (1.0 M, 0.5 ml). After stirring at 0° C. for 2 hours, aqueous sodium hydroxide solution (1.0 M, 5.0 ml) was added carefully. The mixture was extracted with tetrahydrofuran (2×10 ml). The organic phase was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the title compound (0.031 g, 87% yield) as a white powder. 1H NMR (DMSO-d6) δ 3.88 (s, 3H, CH3), 4.44 (d, 2H, J=5.7 Hz, CH2), 5.06 (t, 1H, J=5.7 Hz, OH), 6.29 (s, 2H, NH2), 6.72 (s, 1H, Ar), 7.17 (d, 1H, J=8.9 Hz, Ar), 7.23 (d, 2H, J=8.5 Hz, Ar), 7.45 (dd, 1H, J=8.9 Hz, J=2.8 Hz, Ar), 7.70 (d, 2H, J=8.5 Hz, Ar), 7.91 (d, 1H, J=2.8 Hz, Ar), 9.20 (s, 1H, NH).

Workup

extractionThe mixture was extracted with tetrahydrofuran (2×10 ml)
washThe organic phase was washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-a23428433644469ea40d57178fc0f36a
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419984B2

Reaction notes

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