1,2-Dimethoxyethane → HCID 59272360, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium carbonate (0.636 g, 6.00 mmol), palladium tetrakistriphenylphosphine (0.185 g, 0.160 mmol), pyrimidin-5-ylboronic acid (0.322 g, 2.60 mmol) and 2′-bromo-7′-methoxy-5-methyl-5H-spiro[oxazole-4,9′-xanthen]-2-amine (0.750 g, 1.999 mmol) in a resealable pressure tube, was added DME (6 mL) and water (2 mL) at RT. The tube was sealed and heated to 85° C. After 2 hrs, the mixture was cooled to RT, diluted with EtOAc, and washed with brine. The organic fraction was dried with sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography using 2-8% MeOH in CH2Cl2 with 1% NH4OH to afford a mixture of diastereomers as an off-white foam. [email protected] min. Purification of the resulting racemic product mixture using Chiralpack AD-H (2×15 cm) 30% MeOH/CO2, 100 bar, 70 ml/min afforded:

Provenance & Evidence