(S)-tert-butyl 4-(4-(5-bromopyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 4-(4-(5-tert-butylpyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1187774노트

반응식

HRID 1187774 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][CH2:14][C@H:15]3[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[N:16]3[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Br-].[C:32]([Zn+])([CH3:35])([CH3:34])[CH3:33]>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:32]([C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][CH2:14][C@H:15]3[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[N:16]3[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:11][CH:10]=2)=[N:6][CH:7]=1)([CH3:35])([CH3:34])[CH3:33]

참가 물질

5

반응물 2

HCID 67501307(S)-tert-butyl 4-(4-(5-bromopyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylateHCID 178455669HCID 178455669, 화합물

생성물 1

HCID 67502410(S)-tert-butyl 4-(4-(5-tert-butylpyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate수율 9%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
22 °C

실험 절차

To (S)-tert-butyl 4-(4-(5-bromopyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate (100 mg) and bis(tri-t-butylphosphine)palladium(0) (21.4 mg) in THF (10 ml) under argon was added tert-butylzinc(II) bromide (1.26 ml, 0.5 M solution in THF). The reaction mixture was stirred at 22° C. for 1 hour. The reaction was quenched by addition of EtOAc then washed sequentially with saturated aqueous ammonium chloride solution and 1 N aqueous sodium bicarbonate solution. The phases were separated and the organic phase was dried over MgSO4, filtered and then concentrated in vacuo. The crude material was purified by preparative HPLC (Column: Zorbax 5 micron C18 50×20, flow rate: 30 ml/min; eluant gradient: water (+0.1% formic acid)/acetonitrile (80%-20% to 5%-95%)) to afford (S)-tert-butyl 4-(4-(5-tert-butylpyrimidin-2-ylamino)phenethyl)-2,2-dimethyloxazolidine-3-carboxylate (8.4 mg, 9%) as a yellow oil. MS (ISP): 455.5 ([M+H]+).

후처리

  1. customThe reaction was quenched by addition of EtOAc
  2. washthen washed sequentially with saturated aqueous ammonium chloride solution and 1 N aqueous sodium bicarbonate solution
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by preparative HPLC (Column: Zorbax 5 micron C18 50×20, flow rate: 30 ml/min; eluant gradient: water (+0.1% formic acid)/acetonitrile (80%-20% to 5%-95%))

출처 및 근거

ORD 기록
ord-b9072b6d50664f35983ddc40d4476079
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673950B2

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