Benzyl Alcohol → HCID 68823165, compound

HRID 2053092Notes

Reaction equation

HRID 2053092 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:15]=[C:14]([S:28][CH3:29])[N:13]=1>O1CCCC1>[CH2:3]([O:10][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:15]=[C:14]([S:28][CH3:29])[N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 866125004-Chloro-2-methylthio-6-(3-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 68823165HCID 68823165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of sodium hydride (630 mg, 60% dispersion in mineral oil) in tetrahydrofuran (20 ml) at 0° C. was added benzyl alcohol (1.09 ml). The mixture was stirred for 15 minutes then a solution of 4-chloro-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidine (1.6 g) in tetrahydrofuran (14 ml) was added dropwise. The reaction was allowed to warm to room temperature and stirred for two hours. Solvent was evaporated under reduced pressure and the remaining residue dissolved in dichloromethane (200 ml) and washed with water (2×150 ml). Organics were separated, dried over sodium sulphate and solvent was removed under reduced pressure to yield crude product (2.5 g). Flash chromatography on silica yielded product 4-benzyloxy-2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidine (1.75 g) as a yellow solid.

Workup

  1. stirringstirred for two hours
  2. customSolvent was evaporated under reduced pressure
  3. dissolutionthe remaining residue dissolved in dichloromethane (200 ml)
  4. washwashed with water (2×150 ml)
  5. customOrganics were separated
  6. dry with materialdried over sodium sulphate and solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-d4a54dddf3a84c44a9fb40b6743c2292
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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