Triethylamine → HCID 70418443, compound

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].Cl.[C:21]1([C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH3:30])[CH2:28][NH2:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[C:31]1([C:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:30])[CH2:28][NH:29][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

Procedure

A mixture of 6-chloro-9-β-D-ribofuranosylpurine (2.32 g, 8.09 mmol), 2,2-diphenylpropylamine hydrochloride (2.01 g, 100 mol %), and triethylamine (2.3 mL, 204 mol %) in N,N-dimethylformamide (30 mL) is stirred under nitrogen at room temperature for 19 days, filtered, the solid is washed with ether, and the filtrate is evaporated to an oil. The oil is purified by column chromatography over silica gel, eluting with 5/1 chloroform/methanol, and the appropriate fractions are evaporated to afford N6 -(2,2-diphenylpropyl)adenosine as a foam which retains one-half mole of N,N-dimethylformamide.