Benzylamine → HCID 18507316, compound

HRID 1355846Notes

Reaction equation

HRID 1355846 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([N+:16]([O-:18])=[O:17])=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCOCC1>[CH2:24]([NH:31][C:6]1[C:5]([N+:16]([O-:18])=[O:17])=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=[C:2]([NH2:1])[N:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 86583748Trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-nitro-pyrimidin-4-yl ester

Product 1

HCID 18507316HCID 18507316, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 335 mg (0.95 mmol) trifluoro-methanesulfonic acid 2-amino-6-furan-2-yl-5-nitro-pyrimidin-4-yl ester in 20 ml dioxane was added 1.03 ml (9.46 mmol) benzylamine and the mixture heated at reflux for 1 hour. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate) followed by recrystallisation from ether/hexane afforded 230 mg (78%) N4-benzyl-6-furan-2-yl-5-nitro-pyrimidine-2,4-diamine as a yellow crystalline solid. ES-MS m/e (%): 312 (M+H+, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customChromatography (ethyl acetate) followed by recrystallisation from ether/hexane

Sources & evidence

ORD record
ord-cc56afd6de684d69a94fbbcdda1dadc7
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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