Water → HCID 86696696、化合物

HRID 1774195ノート

反応式

HRID 1774195 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Li]C(C)(C)C.[Si:14]([O:21][CH2:22][C@@H:23]([N:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][N:41]=[C:40](S(C)(=O)=O)[N:39]=2)=[CH:34][C:33]1=[O:48])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([F:31])[CH:25]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>C1COCC1>[Si:14]([O:21][CH2:22][C@@H:23]([N:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][N:41]=[C:40]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)[N:39]=2)=[CH:34][C:33]1=[O:48])[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([F:31])[CH:25]=1)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 962WaterHCID 7286704-Amino-2-methylpyridineHCID 71727006(S)-1-(2-((tert-Butyldimethylsilyl)oxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-oneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 86696696HCID 86696696、化合物収率 38%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

2-Methylpyridin-4-amine (0.28 g, 2.6 mmol) was placed in THF (5 mL) and cooled to −78° C. t-BuLi (1.5 mL, 2.6 mmol) was added dropwise, and the solution was warmed to 0° C. for 30 minutes. This solution was then added dropwise to a −78° C. THF solution (5 mL) of (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (0.070 g, 0.13 mmol). The reaction was stirred for an additional 30 minutes at −78° C., then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by column chromatography (500:10-500:20 DCM/MeOH) to give the product (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-((2-methylpyridin-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.028 g, 38% yield).

後処理

  1. additionwas added dropwise
  2. additionThis solution was then added dropwise to a −78° C
  3. extractionextracted with DCM
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by column chromatography (500:10-500:20 DCM/MeOH)

出典と根拠

ORDレコード
ord-ff2b0e717d8046a696253cca7eaa3580
出典データセット
uspto-grants-2016_02
特許番号
US09259470B2

反応ノート

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