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Sodium hydride → HCID 86619878、化合物

HRID 1024897
ノート
印刷プレビュー

反応式

HRID 1024897 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=1.[OH:19][C@@H:20]1[CH2:24][O:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1.[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=2[F:18])[N:3]=[C:2]([O:19][C@@H:20]2[CH2:24][O:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]2)[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 7062393(R)-tert-butyl 5-hydroxyisoxazolidine-2-carboxylateHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

生成物 1

HCID 86619878HCID 86619878、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of Example 1, step ii) (0.25 g) and 1,1-dimethylethyl (S)-4-hydroxyisoxazolidine-2-carboxylate (0.16 g) in dry THF (5 mL) was added 60% Sodium hydride (0.034 g) over 5 min. The reaction mixture was stirred and heated at 60° C. for 7 days, 1120 was added and the solvents were partially evaporated. The residue was extracted with EtOAc which was washed with H2O, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with Et2O/iso-hexane (1:9) to give the subtitle compound as a gum. Yield: 0.15 g.

後処理

  1. addition1120 was added
  2. customthe solvents were partially evaporated
  3. extractionThe residue was extracted with EtOAc which
  4. washwas washed with H2O
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with Et2O/iso-hexane (1:9)

出典と根拠

ORDレコード
ord-4edeab0830ab4368940e301535cf490a
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722883B2

反応ノート

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