Water → HCID 58641652, compound

HRID 639395Notes

Reaction equation

HRID 639395 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:12]=[N:11][N:10]([CH3:21])[C:9]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178477997HCID 178477997, compound

Product 1

HCID 58641652HCID 58641652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 1 g (3.07 mMol) of 2-chloro-4-[3-(2,4-dichloro-phenyl)-1H-pyrazol-4-yl]-pyrimidine in 10 mL of DMF is added 0.467 g (3.38 mMol) of potassium carbonate at rt under an atmosphere of Argon. After stirring for 30 min, 1.15 mL (18.42 mMol) of methyl iodide is added. After completion of the reaction (28 h), the mixture is poured onto 100 mL of water, and extracted repeatedly with ethyl acetate. The combined organic layers are washed with NaHCO3, water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product is purified twice over silica gel, eluting with ethyl acetate/hexanes (1:1) and CH2Cl2/MeOH (99:1) to obtain the title compound as orange crystals; m.p. 122-125° C.; TLC (silica gel) Rf=0.19 (CH2Cl2/MeOH 99:1).

Workup

  1. customAfter completion of the reaction (28 h)
  2. extractionextracted repeatedly with ethyl acetate
  3. washThe combined organic layers are washed with NaHCO3, water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified twice over silica gel
  8. washeluting with ethyl acetate/hexanes (1:1) and CH2Cl2/MeOH (99:1)

Sources & evidence

ORD record
ord-f8600fa590d34108ac9b1d4d7d34fe8a
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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