Aluminium lithium hydride → 3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzaldehyde
Reaction equation
CON(C)[C:4](=[O:32])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:25]([C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[CH:4]=[O:32])[CH:17]=2)=[CH:24][CH:23]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1Participants
4
Conditions
- Temperature
- -60 °C
Procedure
To a stirred solution of N-methoxy-N-methyl-3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzamide (0.75 g, 1.7 mmol) in THF (10 mL) was added LAH (3.4 mL, 3.4 mmol, 1 M solution in THF) at −60° C. The reaction mixture was stirred at −60° C. for 1 h, was quenched with Na2SO4 solution (2 mL) and was extracted with ethyl acetate (10 mL). The organic layer was separated and washed with water (2 mL) and with brine solution (2 mL) and was dried over anhydrous Na2SO4. Filtration followed by concentration under reduced pressure gave a residue that was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1) to give 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)benzaldehyde (0.6 g, 92%) as an off yellow solid.
Workup
- customwas quenched with Na2SO4 solution (2 mL)
- extractionwas extracted with ethyl acetate (10 mL)
- customThe organic layer was separated
- washwashed with water (2 mL) and with brine solution (2 mL)
- dry with materialwas dried over anhydrous Na2SO4
- filtrationFiltration
- concentrationfollowed by concentration under reduced pressure
- customgave a residue that
- customwas purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1)
Sources & evidence
- ORD record
- ord-b8b8481ada124366985a4aa2722603be
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040541B2
Reaction notes
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