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

HRID 872068ノート

反応式

HRID 872068 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ef668a5f107a4b8ca7fcc0b2709c4cf5
出典データセット
uspto-grants-2015_03
特許番号
US08975261B2

反応ノート

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