(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 1187774ノート

反応式

HRID 1187774 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

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]+).

後処理

  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%))

出典と根拠

ORDレコード
ord-b9072b6d50664f35983ddc40d4476079
出典データセット
uspto-grants-2014_03
特許番号
US08673950B2

反応ノート

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