4-Fluorobenzylamine → 6-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid 4-fluoro-benzylamide

HRID 458694Notes

Reaction equation

HRID 458694 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]2[NH:16][C:15](=[O:17])[CH2:14][N:9]2[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C(O)C.CN(C)C=O>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:4]([C:6]2[N:7]=[C:8]3[NH:16][C:15](=[O:17])[CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[OH:12])=[O:5])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 673264-FluorobenzylamineHCID 1359709526-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl ester

Product 1

HCID 1355082456-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid 4-fluoro-benzylamideYield 34.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of intermediate 5, 6-hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl ester, (0.035 g, 0.146 mmol) and 4-fluorobenzylamine (0.11 g, 0.88 mmol) in anhydrous ethyl alcohol (5 ml) and N,N-dimethylformamide (2 ml) was heated under reflux for 18 h. The solvent was then evaporated in vacuo and the residue was partitioned between ethyl acetate and 0.1 N hydrochloric acid. The organic phase was washed with water and brine then dried over anhydrous sodium sulfate. Evaporation of the solvent and recrystallization of the resulting solid from ethanol gave 0.016 g (34% yield) of the title amide as white crystals. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 4.46 (4H, broad s, 2×CH2), 7.17 (2H, m, aromatics), 7.36 (2H, m, aromatics), 9.07 (1H, broad t, NH), 11.8–12.4 (2H, broad, OH and NH). MS (ESI+) m/z 319 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was then evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and 0.1 N hydrochloric acid
  5. washThe organic phase was washed with water and brine
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. customEvaporation of the solvent and recrystallization of the resulting solid from ethanol

Sources & evidence

ORD record
ord-30747c6ecbf541e0b2b443300b9fb58d
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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