Water → HCID 57419283, compound

HRID 2353057Notes

Reaction equation

HRID 2353057 reaction equation
[F:1][CH:2]([F:14])[C:3]1[NH:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[H-].[Na+].Cl[C:18]1[N:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[N:19]=1.O>CN(C=O)C>[F:14][CH:2]([F:1])[C:3]1[N:7]([C:18]2[N:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[N:19]=2)[C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:5]=2[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 773782,4,6-TrichloropyrimidineHCID 178488965HCID 178488965, compound

Product 1

HCID 57419283HCID 57419283, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Difluoromethyl-4-methoxybenzimidazole (9.03 g, 45.6 mmol) was dissolved in DMF (100 ml), 60% NaH (1.82 g, 45.6 mmol) was added, and stirred for 30 minutes. The reaction mixture was added to a solution obtained by dissolving 2,4,6-trichloropyrimidine (15.7 g, 92.1 mmol) into DMF (100 ml) while cooling with ice, and stirred on an ice bath for 30 minutes and further at room temperature for 2 hours. Water was added to the reaction mixture, precipitated crystals were filtered, and washed well with hexane and ether, then air-dried to afford 2-(2-difluoromethyl-4-methoxybenzimidazol-1-yl)-4,6-dichloropyrimidine (12.3 g, yield 78%).

Workup

  1. additionThe reaction mixture was added to a solution
  2. customobtained
  3. temperaturewhile cooling with ice
  4. stirringstirred on an ice bath for 30 minutes and further at room temperature for 2 hours
  5. customprecipitated crystals
  6. filtrationwere filtered
  7. washwashed well with hexane and ether
  8. customair-dried

Sources & evidence

ORD record
ord-1d64398ca44f40a69a387edf035f4d25
Source dataset
uspto-grants-2010_07
Patent number
US07750001B2

Reaction notes

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