Sodium hydride → (2R,3R)-3-(5-bromo-2-chloropyrimidin-4-yloxy)butan-2-ol

HRID 272631

反応式

HRID 272631 の反応式
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[H-].[Na+].[Br:9][C:10]1[C:11](Cl)=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1>C1COCC1>[Br:9][C:10]1[C:11]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 225936(2R,3R)-ButanediolHCID 2899735-Bromo-2,4-dichloropyrimidine

生成物 1

HCID 59674033(2R,3R)-3-(5-bromo-2-chloropyrimidin-4-yloxy)butan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 1.35 g (15.0 mmol) of (R,R)-(−)-2,3-butanediol in 50 ml of THF is mixed at 0° C. in portions with 480 mg (11.0 mmol) of sodium hydride (55% dispersion) and then stirred for 10 minutes at room temperature. The solution that is produced is added at 0° C. to 2.27 g (10.0 mmol) of 5-bromo-2,4-dichloropyrimidine in 25 ml of THF. The batch is slowly heated to room temperature and stirred for 12 hours. The solvent is drawn off, and the residue that is obtained is purified by chromatography (hexane/ethyl acetate 1:1). 2.29 g (8.1 mmol, corresponding to 81% of theory) of the product is obtained.

後処理

  1. customThe solution that is produced
  2. temperatureThe batch is slowly heated to room temperature
  3. stirringstirred for 12 hours
  4. customthe residue that is obtained
  5. customis purified by chromatography (hexane/ethyl acetate 1:1)
  6. custom2.29 g (8.1 mmol, corresponding to 81% of theory) of the product is obtained

出典と根拠

ORDレコード
ord-cf5b90ba18e04d03aa37097d17d38495
出典データセット
uspto-grants-2008_11
特許番号
US07456191B2

関連ノート

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