m-Chloroperbenzoic acid → N-(3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide

HRID 527422ノート

反応式

HRID 527422 の反応式
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=[O:13])[N:9]([C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH:22]=[CH2:23])[CH:17]=[CH:18][CH:19]=3)[C:7]=2[N:8]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10](=[O:13])[N:9]([C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:24])[CH:22]=[CH2:23])[CH:17]=[CH:18][CH:19]=3)[C:7]=2[N:8]=1)=[O:33]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 86732032N-(3-(2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide

生成物 1

HCID 86732033N-(3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide収率 84.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

At 0° C., to a suspension of N-(3-(2-(methylthio)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (11a) (450 mg, 1.33 mmol) in 25 mL of DCM was added MCPBA (319 mg of 77% max. from Aldrich, 1.42 mmol). After the reaction mixture was stirred at 0° C. for 35 min, it was diluted with 100 mL of DCM, washed with 20 mL of ice cold sat Na2CO3 solution. The DCM layer was dried over Na2SO4 and concentrated to give N-(3-(2-(methylsulfinyl)-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)phenyl)acrylamide (11b) (398 mg, 84% yield) as an off white crystalline solid. The crude material was used in next step without further purification. m/z (ESI, +ve ion) 355.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) 6 ppm 10.36 (1H, s), 9.30 (1H, s), 8.20 (1H, d, J=9.6 Hz), 7.76 (1H, m), 7.69 (1H, m), 7.51 (1H, t, J=8.0 Hz), 7.06 (1H, d, J=7.6 Hz), 6.94 (1H, m), 6.45 (1H, dd, J=16.9, 10.1 Hz), 6.26 (1H, d, J=16.8 Hz), 5.79 (1H, m), 2.72 (3H, s)

後処理

  1. washwashed with 20 mL of ice cold
  2. dry with materialThe DCM layer was dried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-c044157639b64b40a75abc313bac9483
出典データセット
uspto-grants-2016_05
特許番号
US09346801B2

反応ノート

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