Sodium hydride → 2-Chloro-4-(4-chlorophenyl)-5-(cyclopropylmethoxy)pyrimidine

HRID 1528357Notes

Reaction equation

HRID 1528357 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:12](F)=[CH:11][N:10]=1>CN(C)C=O>[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:12]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 79072851HCID 79072851, compound

Product 1

HCID 866631362-Chloro-4-(4-chlorophenyl)-5-(cyclopropylmethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.948 mL cyclopropanemethanol in 13 mL dimethylformamide was added 0.468 g sodium hydride 55% in mineral oil and the reaction mixture was stirred at room temperature for 15 min. The resulting solution was added drop wise to a solution of 2.586 g 2-chloro-4-(4-chloro-phenyl)-5-fluoro-pyrimidine at 0° C. and the mixture was stirred at 0° C. for 30 min. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=10:90 to 80:20 to yield 2.50 g of the title compound as white solid, MS 295.2 (M+H)+.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-8b90c20624514e7d8a07ee645a0febad
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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