Ammonium Chloride → N-(5-bromo-3-methyl-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

Sodium 2-methylpropan-2-olate (0.142 g, 1.48 mmol) was combined with compound 4 (0.125 g, 0.493 mmol) and 2,5-dibromo-3-methylpyridine (0.149 g, 0.592 mmol) in 1,4-dioxane (3 ml). The reaction mixture was degassed by bubbling nitrogen through the solution for ˜1 mM, followed by the addition of XANTPHOS (0.0428 g, 0.0740 mmol) and Pd2(dba)3 (0.0339 g, 0.0370 mmol). The reaction was heated to 140° C. using microwave irradiation for 1 hour. The reaction mixture was poured into sat. NH4Cl and extracted with 10% isopropanol/DCM. The organic layer was dried with MgSO4 and concentrated in vacuum. Purification by flash column chromatography, eluting with a gradient of DCM-5% methanol/DCM provided compound 77 as a yellow solid (150 mg, 71%). LCMS-ESI (POS), M/Z, M+1: Found 423.1

Provenance & Evidence