Guanidine → HCID 178468834, compound

HRID 1656566Notes

Reaction equation

HRID 1656566 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]=1

Participants

4

Reactant 2

HCID 3520GuanidineHCID 10826899Ethyl 4-[2-(5-amino-4-cyanofuran-3-yl)ethyl]benzoate

Product 1

HCID 178468834HCID 178468834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 30 hrs
  3. customthe solvent then evaporated in vacuo
  4. customThe residue is chromatographed on silica gel
  5. washeluting with 5:95 methanol

Sources & evidence

ORD record
ord-72a670814b5243518c237d3feb9e283a
Source dataset
uspto-grants-1993_10
Patent number
US05254687

Reaction notes

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