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

HRID 1468779

반응식

HRID 1468779 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 679776501-methyl-2-(piperidin-4-yloxy)-1H-[4,4']bipyrimidinyl-6-one

생성물 1

HCID 866691462-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzaldehyde수율 52.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-0fee3f999b644fa2b2ef5dd27ce5ed67
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006232B2

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