Reaction SMILES: [Cl:1][C:2]1([C:10]2[C:15]([S:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:14][CH:13]=[CH:12][N:11]=2)[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1>C(O)C.[Pd]>[ClH:1].[CH2:17]([S:16][C:15]1[C:10]([CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[N:11][CH:12]=[CH:13][N:14]=1)[CH2:18][CH2:19][CH3:20]
Reactant: CCCCSc1nccnc1C1(Cl)CN2CCC1CC2
Agent: [Pd]
Solvent: CCO
Product: CCCCSc1nccnc1C1CN2CCC1CC2
Product: Cl
Reaction time: 1 h
Yield: 43.8 %

Procedure:
A 1 g sample of 60% NaH dispersion in oil was triturated twice with hexane then suspended in 300 ml of THF. The mixture was treated with 5 ml of butanethiol and after 30 min the mixture was heated to reflux for 45 min. After cooling to ambient temperature, 1.5 g of (7), (0.0063 mol) was added and the reaction was heated to reflux for 1 h. The mixture was diluted with 100 ml of butanethiol and the reaction was heated to reflux overnight. The solvent was removed by distillation, the residue suspended in 50 ml of H2O, and the mixture extracted 3× with 25 ml of CHCl3, the extracts washed with brine, and the solvent evaporated. The brown solid residue was recrystallized from ether to give 1.25 g of 3-(3-butylthiopyrazinyl)-1- azabicyclo[2.2.2]octan-3-ol (29a). NMR ppm (CDCl3) 0.97 (3H, t), 1.19 (1H, t), 1.19 (1H, m), 1.35-1.57 (4H, m), 1.7 (2H, m), 2.21 (1H, m), 2.5-3.02 (6H, m), 3.2 (2H, m), 4.1 (1H, d), 4.5 (1H, m), 8.17 (1H, d), 8.25 (1H, d). A solution of 1.2 g of (29a) (0.0041 mol) in 100 ml of CH2Cl2 was cooled to 0° C. as 0.95 ml of thionyl chloride in 10 ml of CH2Cl2 was added dropwise. The cooling was removed and after 1 h the reaction was heated to reflux for 45 min. After cooling to ambient temperature, the reaction was treated with ice and the solution was made basic with 1 N NaOH. The mixture was extracted 3× with 25 ml of CH2Cl2, the extracts washed with brine, dried, and the solvent evaporated to give a brown liquid. The liquid was purified by radial chromatography eluting with 5% ethanol-0.5% NH4OH-CHCl3 and then 10% ethanol-1% NH4OH-CHCl3 to give 1 g of 3-chloro-3-(3-butylthiopyrazinyl)-1-azabicyclo[2.2.2]octane (29b). NMR ppm (CDCl3) 0.99 (3H, t), 1.5 (3H, m), 1.7 (4H, m), 2.38 (1H, m), 2.7 (2H, m), 2.98 (1H, m), 3.05-3.4 (4H, m), 3.76 (1H, d), 4.19 (1H, d), 8.18 (1H, d), 8.3 (1H, d). A mixture of 1 g of (29b) (0.0032 mol) and 0.4 g of 10% Pd on carbon in 50 ml of ethanol was hydrogenated for 1 h at 60 psi of H2. The catalyst was removed, the solvent was evaporated, the residue suspended in 5 ml of H2O, and the mixture made basic with saturated aqueous K2CO3. The mixture was extracted 3× with 25 ml of CH2Cl2, the extracts dried, and the solvent evaporated. The residue was purified by radial chromatography eluting with 5% ethanol-0.5% NH4OH-CHCl3 and then 10% ethanol-1% NH4OH-CHCl3. The hydrochloride salt (29) crystallized from ethyl acetate to give 0.44 g of a floculant white solid, mp 193°-194° C. NMR ppm (CDCl3) 0.99 (3H, t), 1.5 (2H. m), 1.7 (4H, m), 2.15 (2H, m), 2.5 (1H, m), 3.23 (3H, m), 3.4 (3H, m), 3.64 (2H, m), 4.38 (1H, q), 8.21 (1H, d), 8.31 (1H, d). Anal. C15H23N3S-HCl requires C: 57.40; H: 7.71; N: 13.37%. Found C: 57.14; H: 7.92; N: 13.12%.