Isopropanol → HCID 86619891, compound

HRID 1959051Notes

Reaction equation

HRID 1959051 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.[H-].[Na+].[CH3:21][CH:22]([OH:24])[CH3:23]>>[Cl:8][C:6]1[CH:7]=[C:2]([O:24][CH:22]([CH3:23])[CH3:21])[N:3]=[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:5]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 86619891HCID 86619891, compound

Procedure

To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine ((the product of example 1 step ii), 3 g) in propan-2-ol (20 ml) was added NaH (0.43 g) slowly and the reaction was then allowed to stir overnight at RT. The reaction mixture was then partitioned between DCM (100 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×100 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a pale yellow solid. Yield: 1.8 g

Workup

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

Sources & evidence

ORD record
ord-ab7eecd5270c418d817081fe982abe9d
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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