Cesium carbonate → HCID 67328492, compound

Participants

Reaction Steps

A mixture of 4,5 Bis(diphenyl-phosphino)-9,9-dimethylxanthene [xanthopos](8.6 mg, 0.01488 mmol) and Tris(dibenzylideneacetone)di-palladium(0)[Pd2(dba)3](6.81 mg, 0.00744 mmol) in dry 1,4-dioxane (5 ml) was stirred vigorously and nitrogen was bubbled through the suspension for 30 minutes. 5-Bromo pyrimidine (19.7 mg, 0.1247 mmol), 6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine (35.57 mg, 0.1247 mmol) and dry cesium carbonate (100 mg, 0.31 mmol) was added. Nitrogen was bubbled through for another 30 minutes; the mixture was allowed to reflux overnight. The mixture was cooled, diluted with ethylacetate, water was added and the layers were separated. The aqueous layer was extracted with ethyl acetate and the two organic extracts were combined. The organics were washed with brine, then dried (sodium sulfate), filtered and concentrated under vacuum. Further purification by silica gel chromatography using 5-10% ethyl acetate/hexane as eluent provided [6-(2-Methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-pyrimidin-5-yl-amine [15] as a yellow solid [Yield: 9.75 mg, 21.7%]

Provenance & Evidence