Cesium carbonate → 6-((2-(4-chlorophenylamino)pyrimidin-5-yl)methoxy)quinolin-2(1H)-one

HRID 77452

反応式

HRID 77452 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:20][C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[N:25][CH:26]=1>CN(C=O)C.O>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:24]2[N:23]=[CH:22][C:21]([CH2:20][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]4)=[CH:26][N:25]=2)=[CH:33][CH:32]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 1770652,6-DihydroxyquinolineHCID 866797335-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine

生成物 1

HCID 866797376-((2-(4-chlorophenylamino)pyrimidin-5-yl)methoxy)quinolin-2(1H)-one収率 29.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 6-hydroxyquinolin-2(1H)-one (0.057 g, 0.354 mmol), Cs2CO3 (0.192 g, 0.590 mmol) and 5-(chloromethyl)-N-(4-chlorophenyl)pyrimidin-2-amine (0.1 g, 0.394 mmol) in DMF (2.5 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and the resulting suspension filtered. The bright yellow filter cake was taken up in methanol and the mixture was stirred for 1 h. The suspension was filtered and the yellow solid was washed with methanol and dried. The solid was further stirred in DCM/MeOH for 2 days. The mixture was filtered, and the filter cake washed with methanol and dried to give 6-((2-(4-chlorophenylamino)pyrimidin-5-yl)methoxy)quinolin-2(1H)-one as a brown solid (0.04 g, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.68 (1H, s), 9.95 (1H, s), 8.64 (2H, s), 7.72-7.92 (3H, m), 7.12-7.47 (5H, m), 6.52 (1H, d, J=9.54 Hz), 5.04 (2H, s). LCMS: R.T.=3.77 min; [M+H]+=378.93.

後処理

  1. filtrationthe resulting suspension filtered
  2. stirringthe mixture was stirred for 1 h
  3. filtrationThe suspension was filtered
  4. washthe yellow solid was washed with methanol
  5. customdried
  6. stirringThe solid was further stirred in DCM/MeOH for 2 days
  7. filtrationThe mixture was filtered
  8. washthe filter cake washed with methanol
  9. customdried

出典と根拠

ORDレコード
ord-ec070130bd174e15b0ece54e1cf1b774
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

関連ノート

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