2-Methyl-3-butyn-2-ol → HCID 69286462, compound

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A mixture of compound N-(3-Chloro-4-methoxy-phenyl)-6-(4-iodo-phenoxy)-N′-isopropyl-[1,3,5]triazine-2,4-diamine (0.4 g, 0.78 mmol), triethylamine (0.27 ml, 1.95 mmol) in dimethylformamide (3 mL) was added bis(triphenylphosphine)palladium(II)chloride (27 mg, 0.04 mmol), CuI (15 mg, 0.08 mmol) and 2-methyl-3-butyn-2-ol (0.11 ml, 1.17 mmol). It is stirred under nitrogen atmosphere for 6 hrs. The mixture was then cooled, diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography (10-20% EtOAc-Hexane) to afford the title compound as a pale yellow solid (0.256 g, 70%). mp 138-140° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 254 nm, Rt 16.80 min, 97.77% purity; MS (CI): m/z 468 (M+H, 100).

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