Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one

HRID 539060

反応式

HRID 539060 の反応式
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8](Cl)=[N:7][C:6]=12.[CH2:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1)[CH2:13][CH3:14].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:16]3[C@@H:15]([CH2:12][CH2:13][CH3:14])[CH2:19][O:18][C:17]3=[O:20])=[N:7][C:6]=12

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8063309AG-E-14754HCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

生成物 1

HCID 67034378(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid.

後処理

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by normal phase column chromatography
  3. washeluting with 1-10% EtOAc/dichloromethane

出典と根拠

ORDレコード
ord-e0476fbd87bc4675ab7a577312b0771f
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

関連ノート

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