N-(tert-Butoxycarbonyl)-1,5-diaminopentane → HCID 58016917, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1.00 g (3.0 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine in 5 ml DMF and add 1.15 g (8.9 mmol) DIEA. Add 1.20 g (5.9 mmol) 5-[(tert.-butyloxycarbonyl)amino]-1-pentylamine [obtainable from 1,5-diaminopentane according to J. Med. Chem. 47 (20), 4933-4940 (2004)] and then heat the mixture to 80° C. for 3 h. After cooling, dilute the mixture with dichloromethane and wash successively with water and saturated sodium chloride solution. Dry the organic phase over magnesium sulphate and concentrate by evaporation. Purify the residue by RP-HPLC (column: Gromsil 250 mm×30 mm, 10 μm; acetonitrile/water gradient: 0-3 min 5% acetonitrile, 3-50 min 5%→98% acetonitrile, 50-55 min 98% acetonitrile). A total of 1.07 g (67% of theor.) of tert.-butyl-(5-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}pentyl)carbamate is obtained in two fractions, in the form of beige crystals.

Provenance & Evidence