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

HRID 74940노트

반응식

HRID 74940 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 (120 g silica gel column).

후처리

  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 (120 g silica gel column)

출처 및 근거

ORD 기록
ord-f6694c669f1f40aa967a6ec15e78555d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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