Potassium Carbonate → 2-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde

HRID 1468779

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.F[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH:25]=[O:26].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[CH:25]=[O:26])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (1.00 g, 3.48 mmol) and 2-fluorobenzaldehyde (475 mg, 3.83 mmol) in dimethyl sulfoxide (3.50 ml) was added potassium carbonate (1.44 g, 10.4 mmol). The mixture was stirred at 120° C. for 4 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde as a yellow solid (711 mg, 1.82 mmol, 52%).

Workup

customThe mixture was partitioned between water and chloroform
washThe organic layer was washed with water (three times)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record: ord-0fee3f999b644fa2b2ef5dd27ce5ed67
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006232B2

Linked notes

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