Ethyl Acetate → (3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanol

HRID 526965ノート

反応式

HRID 526965 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10]2)[C:5]([F:16])=[CH:4][N:3]=1.[CH3:17][Mg]Br.[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11]([CH3:17])([OH:15])[CH2:10]2)[C:5]([F:16])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 86667417(S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanoneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 86667419(3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-methylcyclohexanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone (1.83 g, 7.49 mmol) in THF (100 mL) was added methylmagnesium bromide (21.4 ml of 1.4M solution, 29.96 mmol) at room temperature. The reaction mixture was stirred at room temperature for 5 minutes. To the reaction mixture was added aqueous saturated NH4Cl solution and EtOAc. The organic phase was washed with brine and dried with MgSO4, filtered and concentrated in vacuo. The two spots were separated by silica gel chromatography (120g silica gel column).

後処理

  1. washThe organic phase was washed with brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe two spots were separated by silica gel chromatography (120g silica gel column)

出典と根拠

ORDレコード
ord-de203dd7e5ed41a684a8e8a6c3f7f7c9
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

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