Cesium carbonate → HCID 53379317, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 0.05 g (0.26 mmol) 4-trifluoromethylphenylboronic acid, 0.02 g (0.009 mmol Pd EN Cat™ 30, and 0.65 mL 1 M aq Cs2CO3, was added a solution of 0.005 g (0.009 mmol) 1,1′-(bisdiphenylphosphino)ferrocene and 0.03 g (0.17 mmol) 2-chloro-4,5-dimethoxy-pyrimidine in 1 mL THF. The resulting mixture was heated by microwave to 150° C. for 10 minutes. After cooling, the aq layer was removed and the organic phase was filtered and concentrated. To the resulting residue was added 1 mL 33% HBr in AcOH, and the resulting mixture was heated by microwave to 160° C. for 5 min. The resulting solution was diluted with water (2 mL) and loaded onto an SCX column. After washing with MeOH (5 mL), the crude product was eluted off with 2 M ammonia in MeOH. Purification by automated mass-guided HPLC afforded 1.7 mg (4%) 5-hydroxy-2-(4-trifluoromethyl-phenyl)-3H-pyrimidin-4-one. NMR (499 MHz, DMSO-d6): δ 9.85 (br s, 1H); 8.22 (d, J=7.93 Hz, 2H); 7.85 (d, J=8.12 Hz, 2H); 7.63 (br s, 1H). High resolution mass spec (FT/ICR) calc (M+H)+=257.0533 found 257.0532.

Provenance & Evidence