Sodium hydride → (2R,3R)-3-([6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)butan-2-ol

HRID 1958892Notes

Reaction equation

HRID 1958892 reaction equation
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[Cl:7][C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:9]=1.[H-].[Na+]>O1CCCC1>[Cl:7][C:8]1[N:9]=[C:10]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:11]=[C:12]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])[CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 225936(2R,3R)-ButanediolHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 86619864(2R,3R)-3-([6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)butan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3R)-butane-2,3-diol (250 mg) and 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step (ii)) (427 mg) in anhydrous tetrahydrofuran (20 ml) at ambient temperature was added 60% sodium hydride (33.4 mg). After stirring for 15 minutes the reaction mixture was partitioned between aq. ammonium chloride solution and ethyl acetate. The organics collected, dried (MgSO4) and solvents removed under vacuo to give the subtitle compound as colourless gum. Yield: 525 mg.

Workup

  1. customwas partitioned between aq. ammonium chloride solution and ethyl acetate
  2. dry with materialThe organics collected, dried (MgSO4) and solvents
  3. customremoved under vacuo

Sources & evidence

ORD record
ord-26b3e38b193f4a30ac594a1b3ff91523
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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