N,N,N',N'-Tetramethylethylenediamine → HCID 58233781, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromospiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexan]-3-amine (44) (0.233 g, 0.673 mmol), Zn(CN)2 (0.0474 g, 0.404 mmol), and TMEDA (0.0202 ml, 0.135 mmol), in DMF (2 mL) was degassed by bubbling nitrogen through the solution for ˜1 min before adding Pd2(dba)3 (0.0462 g, 0.0505 mmol), and Xantphos (4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene, 0.0584 g, 0.101 mmol). The mixture was heated to 160° C. for 5 min with microwave irradiation. The reaction mixture was diluted in water and extracted with 10% iPrOH/DCM (3×75 ml). The organic layer was dried with MgSO4 and concentrated in vacuo. Purification on a 40 g combiflash column [(dry loaded), eluting with 50% EtOAc:Hexane to 100% EtOAc then with 4% MeOH/36% DCM/EtOAc] afforded 3-aminospiro[chromeno[3,4-d]pyrimidine-5,1′-cyclohexane]-7-carbonitrile (47) as a white solid (0.133 g, 68%). LCMS-ESI (POS), M/Z, M+1: Found 293.0.

Provenance & Evidence