Tetrahydrofuran → 5-bromo-4-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidine

HRID 872068노트

반응식

HRID 872068 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[CH2:13][C@@H:12]2[CH2:14][OH:15])=[N:9][CH:10]=1.[Br:16][C:17]1[C:18](Cl)=[N:19][C:20](Cl)=[N:21][CH:22]=1.[CH2:25]1COCC1>>[Br:16][C:17]1[C:18]([O:15][CH2:14][C@H:12]2[CH2:13][C@@H:11]2[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][N:9]=2)=[N:19][C:20]([CH3:25])=[N:21][CH:22]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 66834134((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methanol

생성물 1

HCID 710613855-bromo-4-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidine

실험 절차

NaH (78 mg, 1.95 mmol, 60% disp.) was added to a stirring solution of [(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methanol (S,S-DD3, ent2) (350 mg, 1.953 mmol) and 5-bromo-2,4-dichloropyrimidine (445 mg, 1.953 mmol) in THF (9.77 mL). The reaction mixture was stirred at room temperature for 1 hour, and then quenched by dropwise addition of saturated aqueous NaHCO3. The reaction mixture was diluted with EtOAc (50 mL), and washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL). The organics were dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an orange gum. The unpurified product was sufficiently pure to use in the subsequent step without further purification. LRMS m/z (M+H) 372.2 found, 372.0 required.

후처리

  1. customquenched by dropwise addition of saturated aqueous NaHCO3
  2. additionThe reaction mixture was diluted with EtOAc (50 mL)
  3. washwashed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ef668a5f107a4b8ca7fcc0b2709c4cf5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975261B2

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