[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:3][CH:2]=1.[CH:18]([N-]C(C)C)(C)C.[Li+].IC.O>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][C:10]([CH3:18])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:3][CH:2]=1
1-(4-pyrimidinyl)-4-(ethoxycarbonyl)piperidine (400 mg) in 4 ml tetrahydrofuran was cooled to -70° C and treated with a solution of lithium diisopropylamide (1.0 ml in THF), under an argon atmosphere. After stirring 1.5 hours 1.2 ml of a solution of 1 ml iodomethane in 10 ml THF was added and reaction mixture left to reach room temperature overnight. Water added and extracted twice with ethyl acetate. Organic extract washed with brine and dried over magnesium sulphate, filtered and evaporated to give 1-(4-pyrimidinyl)-4-methyl-4-(ethoxycarbonyl)piperidine (370 mg) as an oil; NMR (CDCl3): 1.24 (s, 3H), 1.28 (t, 3H), 1.38-1.51 (m,2H), 2.14-2.26 (m, 2H), 3.12-3.26 (m, 2H), 4.03-4.14 (m, 2H), 4.2(q,2H), 6.5 (dd, 1H), 8.17 (d. 1H), 8.57 (s, 1H)
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