Dimethylformamide → HCID 58088120, compound

Participants

Reaction Steps

To (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.9 g, 3.93 mmol) in N,N-dimethylformamide (20 mL) was added Cs2CO3 (2.69 g, 8.25 mmol) and dimethyl 6-chloropyrimidin-4-ylcarbonimidodithioate (0.964 g, 4.12 mmol). The suspension was stirred at room temperature for 18 hours, then heated at 100 C for 3 hours. The mixture was concentrated and purified by silica gel chromatography (5-15% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford (R)—N-(6-(methylthio)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.21 g, 0.72 mmol, 48.2% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.43 (1 H, br. s.), 8.55 (1 H, d), 6.78 (1 H, br. s.), 3.98 (1 H, d), 3.64 (1 H, d), 3.37 (1 H, dd), 2.72-3.06 (5 H, m), 2.51 (3 H, s), 2.08-2.24 (2 H, m), 1.69-1.81 (1 H, m), 1.41-1.64 (2 H, m). LCMS R.T.=0.93; [M+H]+=306.29.

Provenance & Evidence