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

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid (200 mg, 1.02 mmol) and DIPEA (0.43 mL) in DMF (100 mL) is added TBTU (395 mg, 1.23 mmol). The reaction mixture is stirred at 0° C. for 15 min before adding 4-benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide. Stirring is continued for 1 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. phases are dried over MgSO4, filtered and evaporated to give a brown oil. The oil is dissolved in THF (5.0 mL) and Burgess reagent (155 mg, 0.65 mmol) is added. The reaction mixture is heated to 110° C. for 15 min under microwave conditions. The reaction mixture is evaporated and purified by prep. TLC (eluting with Heptane/EA 9:1) to afford {4-[5-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,3,4]oxadiazol-2-yl]-6-methyl-pyrimidin-2-yl}-isopropyl-amine as a yellow oil (125 mg, 56%); LC-MS: tR=1.16; [M+H]+=444.08.

Provenance & Evidence