Vertellus → 4-Pyrimidinebutanol,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-

HRID 16462

反応式

HRID 16462 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11](OCC)=[O:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1.[B-].[Na+]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]4[NH:30][CH:31]=[CH:32][C:25]=34)=[C:19]([F:33])[CH:18]=2)[N:3]=1

参加物

4

反応物 2

HCID 22959485VertellusHCID 587333944-Pyrimidinebutanoic acid,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-,ethyl ester

生成物 1

HCID 179792724-Pyrimidinebutanol,2-amino-6-[[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino]-

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

300 mg (0.67 mmol) of 4-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butan-1-ol (from example 132) are suspended in 15 ml of ethanol, and 253 mg (6.66 mmol) of sodium borohydrate are added a little at a time at RT. The mixture is stirred at RT for 24 hours and then concentrated, and ethyl acetate and water are added. The organic phase is dried over sodium sulfate. The product is purified by column chromatography (silica gel 60; gradient column, mobile phase: DCM:methanol=9:1 to 3:1). 133 mg (27%) of the starting material are recovered. The product fraction is re-purified by preparative HPLC. This gives the title compound.

後処理

  1. concentrationconcentrated
  2. additionethyl acetate and water are added
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe product is purified by column chromatography (silica gel 60; gradient column, mobile phase: DCM:methanol=9:1 to 3:1)
  5. custom133 mg (27%) of the starting material are recovered
  6. customThe product fraction is re-purified by preparative HPLC

出典と根拠

ORDレコード
ord-9bdc979f3ea34dbe87830441684289c4
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

関連ノート

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