Tyramine → HCID 69781830, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) stirred suspension of 1.6 g (6.9 mmol) 2-amino-4-(2-furyl)-6-(methylthio)-5-pyrimidinecarbonitrile in 100 ml dichloromethane was added 3.6 g (20.7 mmol) m-chloroperbenzoic acid (70% purity) and stirring continued for 15 minutes at 0° C. The reaction mixture was then concentrated in vacuo and residue resuspended in 100 ml DME. To this stirred suspension were added 0.47 g (3.4 mmol) tyramine and 1.4 ml (10.3 mmol) DBU and the mixture heated at 100° C. for 1 hour. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether afforded 160 mg (5%) 3-chloro-benzoic acid 4-[2-(2-amino-5-cyano-6-furan-2-yl-pyrimidin-4-ylamino)-ethyl]-phenyl ester as a white crystalline solid. ES-MS m/e (%): 484 (M{37Cl}+Na+, 10), 482 (M{35Cl}+Na+, 25), 462 (M{37Cl}+H+, 35), 460 (M{35Cl}+H+, 100).

Provenance & Evidence