Aluminium lithium hydride → 3-(6-(4-Phenoxyphenylamino)pyrimidin-4-ylamino)benzaldehyde

HRID 929852Notes

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]=1

Participants

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, I 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-2cd1df2785a04873a3e8d1c36071b5f2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296704B2

Reaction notes

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