1,3-Propanediol → 3-({6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propan-1-ol

HRID 1025033Notes

Reaction equation

HRID 1025033 reaction equation
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.[CH2:19]([OH:23])[CH2:20][CH2:21][OH:22].[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:22][CH2:21][CH2:20][CH2:19][OH:23])[CH:7]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 866198943-({6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step ii), 3 g) and propane-1,3-diol (1.1 g) in THF (50 ml) was added NaH (390 mg) slowly and the reaction was then allowed to stir at mom temperature for 18 h. The reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a yellow oil. Yield 2.95

Workup

  1. customThe reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml)
  2. customThe organics were separated
  3. extractionthe aqueous layer was re-extracted with DCM (2×150 ml)
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-f46541ed63894abda53c7e504ab23690
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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