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

HRID 272631

Reaktionsgleichung

Reaktionsgleichung von HRID 272631
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cf5b90ba18e04d03aa37097d17d38495
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456191B2

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