[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]=1Sodium 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.
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