Ammonia → HCID 15126104, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 12 (150 mg) and saturated ethanolic ammonia (50 mL) was heated at 50° C. in a glass-lined stainless steel pressure vessel for 48 hours. The reaction mixture was evaporated to dryness to afford a syrup which was purified on two silica gel thick plates (Analtech, GF, 1000 μm) that were developed in 99:1 CHCl3 -MeOH. The product was eluted with CHCl3 and evaporated. The residue was crystallized from EtOAc-cyclohexane to give pure 15 (125 mg, 86%); mp. 123°-125° C.; FAB MS 524 (M+H)+ ; 1H NMR (CDCl3) δ 8.14 (s, 1, H-8), 7.72 (m, 4, ArH), 7.42 (m, 6, ArH), 6.02 (brs, 2, NH2), 6.16 (m, 1'-H), 3.93 (m, 1, 5'-H), 3.84 (m, 1, 5'-H), 3.73 (m, 1, 4'-H), 2.36 (m, 2, 2'-H), 2.18 (m, 1, 3'-H), 1.90 (m, 1, 3'-H), 1.1 (s, 9, t-butyl).

Provenance & Evidence