Diisopropylethylamine → HCID 68283130, compound

Participants

Reaction Steps

To a solution of pyrimidine-4-carboxylic acid (261 mg, 2.00 mmol) and DIPEA (0.52 mL, 2.96 mmol) in DMF (8 mL) was added methyl isocyanoacetate (0.28 mL, 2.93 mmol) at rt. The resulting yellow solution was stirred at rt for 5 min and cooled to 0° C. DPPA (0.54 mL, 2.43 mmol) was then added and the resulting solution was stirred at 0° C. for 1 h and at rt for 30 min. Aq. sat. NaHCO3-solution was added and the mixture extracted with EtOAc (4×). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification by FC (hept/EtOAc 9:1 to 100% EtOAc) yielded methyl 5-(pyrimidin-4-yl)oxazole-4-carboxylate. LC-MS conditions A: tR=0.68 min, [M+H]+=206.43.

Provenance & Evidence