Sodium hydride → 4-Chloro-6-(1-methyl-2-imidazolylmethoxy)pyrimidine

HRID 2290722Notes

Reaction equation

HRID 2290722 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[CH2:9][OH:10].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:10][CH2:9][C:5]2[N:4]([CH3:3])[CH:8]=[CH:7][N:6]=2)[N:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 573612(1-methyl-1H-imidazol-2-yl)methanol

Product 1

HCID 202301544-Chloro-6-(1-methyl-2-imidazolylmethoxy)pyrimidineYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.30 g as an 80% dispersion by weight in oil) was added to a solution of 1-methyl-2-hydroxymethylimidazole (1.12 g) in tetrahydrofuran (30 ml) and the mixture stirred at room temperature for one hour. A solution of 4,6-dichloropyrimidine (1.48 g) in tetrahydrofuran (10 ml) was added to the reaction mixture dropwise over 30 minutes and the mixture stirred at room temperature for 3 hours and evaporated. The residue was taken up in dichloromethane and the solution extracted into 2M hydrochloric acid. The acidic layer was washed with dichloromethane, basified with saturated aqueous sodium hydrogen carbonate solution and extracted into dichloromethane. The organic layer was dried over Na2SO4 and evaporated to give the title compound (1.2 g), m.p. 126°-128° C. This compound was used directly in subsequent reactions.

Workup

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. customevaporated
  3. extractionthe solution extracted into 2M hydrochloric acid
  4. washThe acidic layer was washed with dichloromethane
  5. extractionextracted into dichloromethane
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-ba7df260f57b4899be3fdebba24f6784
Source dataset
uspto-grants-1986_10
Patent number
US04618609

Reaction notes

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