Sodium hydride → HCID 22288424, compound

HRID 968241Notes

Reaction equation

HRID 968241 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>CN(C=O)C>[CH3:22][S:21][C:17]1[N:18]=[C:19]([N:11]2[CH:10]=[CH:9][N:8]=[C:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:20]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 695912-PhenylimidazoleHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 22288424HCID 22288424, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Phenylimidazole (1-2, 50 g, 347 mmol) was dissolved in 400 ml DMF and the resulting solution was cooled to 0° C. Sodium hydride (8.32 g of solid NaH, plus 13.9 g of a 60% dispersion in mineral oil, 347 mmol) was added and the mixture was stirred for 10 minutes. 4-Chloro-2-(methylthio)pyrimidine (1-1, 55.7 g, 347 mmol) was then added over 2 minutes. The reaction was then heated to 100° C. After stirring overnight the reaction was partitioned between water and EtOAc. The organic phase was washed 2× with water, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (eluting with 50:50 to 70:30 EtOAc/Hexane) afforded 2-(methylthio)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine.

Workup

  1. temperatureThe reaction was then heated to 100° C
  2. stirringAfter stirring overnight the reaction
  3. customwas partitioned between water and EtOAc
  4. washThe organic phase was washed 2× with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washby flash column chromatography (eluting with 50:50 to 70:30 EtOAc/Hexane)

Sources & evidence

ORD record
ord-21eb1bdc209f4a23841e0c35a1208033
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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