Sodium hydride → HCID 67523917, compound

HRID 659019Notes

Reaction equation

HRID 659019 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:13][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 67523917HCID 67523917, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

173 mg (6.85 mmol) 95% sodium hydride was given to a solution of 979 mg (6.23 mmol) 3-fluoro-4-nitrophenol in 10 ml DMF. Stirring was continued for 30 min. at room temperature. 1.00 g (6.23 mmol) 4-chloro-2-methylsulfanyl-pyrimidine was added and the mixture heated to 80° C. for 16 h. The reaction mixture was evaporated, taken up with water and extracted with ethyl acetate. The organic phase was extracted with water, dried (sodium sulphate) and evaporated. The obtained material was dissolved in ethyl acetate and purified by chromatography over silica (ethyl acetate/n-heptane 1:2) to give 570 mg 4-(3-fluoro-4-nitro-phenoxy)-2-methylsulfanyl-pyrimidine.

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase was extracted with water
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. dissolutionThe obtained material was dissolved in ethyl acetate
  7. custompurified by chromatography over silica (ethyl acetate/n-heptane 1:2)

Sources & evidence

ORD record
ord-ec0974a2d91a470dae28eff07096141e
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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