Ammonium Chloride → (7H-Pyrrolo[2,3-d]pyrimidin-4-yl)(o-tolyl)methanone

HRID 1506119ノート

反応式

HRID 1506119 の反応式
C([Mg]Cl)(C)C.I[C:7]1[C:8]2[CH:15]=[CH:14][NH:13][C:9]=2[N:10]=[CH:11][N:12]=1.CC1C=CC=C(C)C=1[Mg]Br.CON(C)[C:29](=[O:37])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:36].[Cl-].[NH4+]>O1CCCC1>[N:10]1[C:9]2[NH:13][CH:14]=[CH:15][C:8]=2[C:7]([C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])=[O:37])=[N:12][CH:11]=1

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 11344340N-methoxy-N,2-dimethylbenzamideHCID 578708044-Iodo-7H-pyrrolo(2,3-d)pyrimidineHCID 178418918HCID 178418918、化合物HCID 178424791HCID 178424791、化合物

生成物 1

HCID 71258405(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)(o-tolyl)methanone収率 68.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Isopropylmagnesium chloride (2.0 M solution in tetrahydrofuran, 1.05 mL, 2.10 mmol) was gradually added dropwise to 4-iodo-7H-pyrrolo[2,3-d]pyrimidine (245 mg, 1.00 mmol) obtained in Reference Synthetic Examplea 1 in tetrahydrofuran (5 mL) cooled to −78° C., and the resulting reaction mixture was stirred at −78° C. for 15 minutes. The reaction mixture was warmed to room temperature and stirred with (2,6-dimethylphenyl)magnesium bromide (1.0 M solution in tetrahydrofuran, 1.1 mL, 1.1 mmol) and N-methoxy-N,2-dimethylbenzamide (180 mg, 1.00 mmol) in tetrahydrofuran (4 mL) at room temperature for one day. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→1/1 (v/v)) to give the title compound as a pale yellow solid (162 mg, yield 68%).

後処理

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was warmed to room temperature
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→1/1 (v/v))

出典と根拠

ORDレコード
ord-c1e715bc70fc4d188613a52317509298
出典データセット
uspto-grants-2015_12
特許番号
US09216999B2

反応ノート

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