1,2-Dichloroethane → {4-[3-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyrimidin-2-yl}-diethyl-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-diethylamino-6-methyl-pyrimidine-4-carboxylic acid (5.56 g, 27.0 mmol mmol) and 4-benzyloxy-3-ethyl-N-hydroxy-5-methyl-benzamidine (7.69 g, 27 mmol) in DMF (80 mL), EDC (6.74 g, 35.2 mmol) and HOBt (4.75 g, 35.2 mmol) are added at 0° C. Stirring is continued at rt for 2 h and the reaction mixture is then diluted with EtOAc and washed with sat. aq. NaHCO3. The aq. phase is extracted with EtOAc and the combined org. extracts are dried over MgSO4, filtered and evaporated to give a brown oil. The oil is dissolved in dioxane (30 mL) and the solution is heated to 85° C. for 18 h. The reaction mixture is evaporated and purified by CC (eluting with Heptane/EA 9:1) to afford {4-[3-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyrimidin-2-yl}-diethyl-amine as a yellow oil (4.3 g, 35%); LC-MS: tR=1.35; [M+H]+=458.48.

Provenance & Evidence