[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([C:15]#[C:16][CH3:17])[CH3:14])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:23]I>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([N:12]([CH3:23])[C:13]([CH3:14])([C:15]#[C:16][CH3:17])[CH3:18])=[O:11])[CH:5]=[N:6][CH:7]=1To a solution of 2-(5-chloro-3-pyridyloxy)-N-(2-methylpent-3-yn-2-yl)butyramide (0.10 g; prepared as described in Example 1) in dry tetrahydrofuran (9 ml) was added sodium hydride (0.011 g) at ambient temperature under an atmosphere of nitrogen. The mixture was stirred for 0.75 hours, a solution of methyl iodide (0.023 ml) in dry tetrahydrofuran was added then the reaction mixture stirred for a further 0.5 hours at ambient temperature. The reaction was diluted with water, extracted with ethyl acetate (three times) and the extracts were combined, washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was fractionated by chromatography (silica:hexane/ethyl acetate, 3:1 by volume) to give the required product as a beige solid, 0.075 g. m.p. 67–68° C. 1H NMR (CDCl3) δ: 1.14 (3H, t); 1.68 (3H, s); 1.69 (3H, s); 1.85 (3H, s); 2.02 (2H, m); 3.20 (3H, s); 4.70 (1H, t); 7.18 (1H, m); 8.18 (1H, m); 8.20 (1H, m).
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