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

HRID 272631

Reaction equation

HRID 272631 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cf5b90ba18e04d03aa37097d17d38495
Source dataset
uspto-grants-2008_11
Patent number
US07456191B2

Linked notes

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