Methyl iodide → N-(3-Chloro-4-fluorophenyl)-7-{(2E)-3-[(2S)-1-methylpyrrolidin-2-yl]prop-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38573ノート

反応式

HRID 38573 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:23](=[O:31])/[CH:24]=[CH:25]/[C@@H:26]5[CH2:30][CH2:29][CH2:28][NH:27]5)[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[C:32](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:23](=[O:31])/[CH:24]=[CH:25]/[C@@H:26]5[CH2:30][CH2:29][CH2:28][N:27]5[CH3:32])[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25222665HCID 25222665、化合物

生成物 1

HCID 25221099N-(3-Chloro-4-fluorophenyl)-7-{(2E)-3-[(2S)-1-methylpyrrolidin-2-yl]prop-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine収率 13%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-(3-Chloro-4-fluorophenyl)-7-{(2E)-3-[(25)-pyrrolidin-2-yl]prop-2-enoyl}-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-amine from Example 13 (60 mg, 0.13 mmol) in DMF (1 mL) was added potassium carbonate (27 mg, 0.20 mmol) and iodomethane (20 mg, 0.14 mmol), and the mixture was stirred overnight at rt. The reaction mixture was diluted with ethyl acetate and extracted with water. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: DCM/MeOH 10:1) to yield 8 mg (13%) of the title compound.

後処理

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by column chromatography on silica gel (eluent: DCM/MeOH 10:1)

出典と根拠

ORDレコード
ord-3e0ac45d4e73494693531e1d3a1c3ce1
出典データセット
uspto-grants-2013_09
特許番号
US08524722B2

反応ノート

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