[Li]C(C)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.Cl([O-])(=O)(=O)=O.[CH2:18]1[C:25]2[CH2:24][CH2:23][CH2:22][N+:21]=2[CH2:20][CH2:19]1.Cl>CCCCC.CCOCC.C1COCC1.CCOCC>[N:9]1[CH:8]=[C:7]([C:25]23[CH2:24][CH2:23][CH2:22][N:21]2[CH2:20][CH2:19][CH2:18]3)[CH:12]=[N:11][CH:10]=1A solution of 1.7M tBuLi (1.6 mL, 2.6 mmol) in pentane was added to 5-bromopyrimidine (190 mg, 1.2 mmol) in Et2O:THF (1:1, 12 mL) at -100° C. After stirring for 10 minutes, 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (500 mg, 2.4 mmol) was added to the reaction slurry, and stirring was continued for 30 minutes. The reaction mixture was then allowed to warm to 0° C. and stir for 1 hour. A solution of 2N HCl was added, and the reaction mixture was poured over Et2O and the phases separated. The aqueous phase was basified with 15% NaOH solution and extracted with CH2Cl2 (2×). The CH2Cl2 phases were combined, dried (MgSO4), concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH, 98:2) to afford a clear oil (40 mg, 18%). MS (CI/NH3) m/e: 190 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.60-1.73 (m, 2H), 1.82-2.11 (m, 6H), 2.66-2.75 (m, 2H), 3.15-3.21 (m, 2H), 8.85 (s, 2H), 9.05 (s,1H).
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