Guanidine → HCID 178468834, compound
Reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[NH2:5][C:6]1O[CH:8]=[C:9]([CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=2)[C:10]=1[C:11]#[N:12]>C(O)C>[NH2:3][C:2]1[NH:4][C:6]2=[N:5][CH:8]=[C:9]([CH2:13][CH2:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[C:10]2=[C:11]([NH2:12])[N:1]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of guanidine free base (prepared from 105 mg of guanidine hydrochloride and 60 mg of sodium ethoxide) in 10 mL of anhydrous ethanol are added 284 mg (1 mmol) of ethyl 4-[2-(2-amino-3-cyanofur-4-yl)ethyl]benzoate. The mixture is heated at reflux for 30 hrs and the solvent then evaporated in vacuo. The residue is chromatographed on silica gel, eluting with 5:95 methanol:methylene chloride, to yield ethyl 4-{2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-5-yl)ethyl}benzoate as a light brown solid; m.p. 202°-204° C. Mass spectrograph calculated for C17H19N5O2 : 325.1538, Found: 325.1543.