4-Fluorobenzylamine → HCID 54680805, compound

HRID 1726909Notes

Reaction equation

HRID 1726909 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][OH:14])[C:5]2=[N:4][C:3]=1[C:15]([O:17]CC)=O.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1>C(O)C.C(OCC)(=O)C>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:15]([C:3]2[N:4]=[C:5]3[N:11]([CH2:12][CH2:13][OH:14])[CH2:10][CH2:9][N:6]3[C:7](=[O:8])[C:2]=2[OH:1])=[O:17])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 673264-FluorobenzylamineHCID 57565063HCID 57565063, compound

Product 1

HCID 54680805HCID 54680805, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 6-hydroxy-1-(2-hydroxyethyl)-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate (0.110 g, 0.408 mmol) and 4-fluorobenzylamine (0.200 g, 1.6 mmol) in anhydrous ethanol (5 ml) was heated under reflux for 6 h. The reaction mixture was then diluted with ethyl acetate, washed successively with 0.1 N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residual solid from ethanol gave 0.116 g (82% yield) of the title amide as white cubes; mp 203° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.54 (2H, t, J=5.0 Hz, CH2), 3.80 (2H, t, J=8.5 Hz, CH2), 3.89 (2H, t, J=5.0 Hz, CH2), 4.15 (2H, t, J=8.5 Hz, CH2), 4.57 (2H, d, J=6.0 Hz, NCH2), 7.07 (2H, m, aromatics), 7.34 (2H, m, aromatics), 7.92 (1H, broad t, NH), 11.68 (1H, s, OH). Anal. Calcd for C16H17FN4O4: C, 55.17; H, 4.92; N, 16.08. Found: C, 55.22; H, 5.06; N, 15.89.

Workup

  1. temperatureunder reflux for 6 h
  2. washwashed successively with 0.1 N hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customCrystallization of the residual solid from ethanol

Sources & evidence

ORD record
ord-cb4bc700d91c431ab4a271e711fcf41b
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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