Sodium Chloride → HCID 18763640, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 100 mg (0.5 mmol) of 2-chloro-4-methyl-6-pyrrolidin-1-yl-pyrimidine in 0.5 ml DMF under an argon atmosphere were added at RT 67 mg (0.25 mmol) tris-(o-tolyl)phosphine, 5.5 mg (0.025 mmol) palladium(II) acetate, 17 mg (0.2 mmol) NaHCO3 followed by 263 mg (2.5 mmol) 2-vinylpyridine. The mixture was heated at 130° C. for 48 h, cooled to RT and 1.5 ml saturated aqueous NaCl solution was added. The mixture was extracted 4-times with 2 ml EtOAc/Et2O (2/1), the combined organic layers were washed with saturated aqueous NaCl, dried over MgSO4 and concentrated in vacuo. The residue was applied to a silica gel column with hexane/EtOAc as eluent (gradient: 1/1 to 1/9). Combination of the purified fractions and concentration in vacuo gave 26 mg (20%) of the desired (E)-4-methyl-2-(2-pyridin-2-yl-vinyl)-6-pyrrolidin-1-yl-pyrimidine as yellow solid. ISP mass spectrum, m/e: 267.3 (M+1 calculated for C16H18N4: 267).

Provenance & Evidence