Sodium hydride → HCID 21833688, compound

HRID 1418709Notes

Reaction equation

HRID 1418709 reaction equation
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[N:4]1.Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1>CN(C)C=O>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[O:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 21833673HCID 21833673, compound

Product 1

HCID 21833688HCID 21833688, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a mixture of 10 ml of anhydrous N,N-dimethylformamide and 96 mg of sodium hydride (60% oil dispersion) was added dropwise an anhydrous N,N-dimethyl-formamide (5 ml) solution of 500 mg of 2-[4-(1-pyrazolyl)methylphenoxy]ethanol (produced in Reference Production Example 1 described below) under stirring over 10 minutes. After stirring at 60° to 70° C. for 2 hours, the mixture was cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (5 ml) solution of 288 mg of 2-chloropyrimidine was added dropwise over 30 minutes. The mixture was then stirred at room temperature overnight and then at 60° to 70° C. for further 2 hours. The reaction mixture was poured into 50 ml of ice water, which was extracted with twice with 30 ml of toluene. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 339 mg of 4-(1-pyrazolyl)methyl-phenyl 2-(2-pyrimidyloxy)ethyl ether (compound 2). Yield, 50%.

Workup

  1. stirringAfter stirring at 60° to 70° C. for 2 hours
  2. additionwas added dropwise over 30 minutes
  3. stirringThe mixture was then stirred at room temperature overnight
  4. waitat 60° to 70° C. for further 2 hours
  5. extractionwas extracted with twice with 30 ml of toluene
  6. washwashed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee766b3b284c46d5857310c1715ae79f
Source dataset
uspto-grants-1999_03
Patent number
US05883262

Reaction notes

Loading…