Water → HCID 59570670, compound

HRID 1961715Notes

Reaction equation

HRID 1961715 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH2:17][OH:18])=[N:6][CH:7]=[C:8]([N:10]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11]2)[N:9]=1.I[CH3:20].O>CS(C)=O.C(OCC)(=O)C.CCCCCCC>[Cl:3][C:4]1[C:5]([CH2:17][O:18][CH3:20])=[N:6][CH:7]=[C:8]([N:10]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11]2)[N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 59570672[3-Chloro-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]-methanol

Product 1

HCID 59570670HCID 59570670, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

Sodium hydride (60% in mineral oil, 18 mg, 0.45 mmol) was added to a solution of [3-chloro-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazin-2-yl]methanol (102 mg, 0.43 mmol) in dimethyl sulfoxide (4 mL) and stirred for 15 minutes. Iodomethane (29 μL, 0.74 mmol) was added and the mixture was stirred at room temperature for 30 minutes and at 50° C. for 30 minutes. Sodium hydride (60% in mineral oil, 50 mg) and iodomethane (200 μL) was added and the mixture was stirred at 50° C. for 30 minutes. After cooling down water was added and a brown solid formed. Filtration followed by re-dissolvation in ethyl acetate, wash with brine, drying over sodium sulphate, filtration and evaporation gave the crude material. Flash chromatography (ethyl acetate/heptane as eluent) gave 3-chloro-5-(3,5-dimethyl-pyrazol-1-yl)-2-methoxymethyl-pyrazine (34 mg, 32%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes and at 50° C. for 30 minutes
  2. stirringthe mixture was stirred at 50° C. for 30 minutes
  3. additionwas added
  4. customa brown solid formed
  5. filtrationFiltration
  6. dissolutionby re-dissolvation in ethyl acetate
  7. washwash with brine
  8. dry with materialdrying over sodium sulphate, filtration and evaporation
  9. customgave the crude material

Sources & evidence

ORD record
ord-0fbb965e178b40888fac45f1b1cba9d5
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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