4-Fluorobenzylamine → HCID 54730366, compound

HRID 222616Notes

Reaction equation

HRID 222616 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[OH:11])=[O:4].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>CO>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:3]([C:5]2[N:6]=[C:7]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:8]3[C:9](=[O:12])[C:10]=2[OH:11])=[O:4])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 57494523HCID 57494523, compound

Product 1

HCID 54730366HCID 54730366, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Bromo-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid methyl ester (20 mg, 0.07 mmol) and p-fluorobenzylamine (19 uL, 0.17 mmol) in dry methanol (4 mL) was heated to reflux with stirring. Reaction progress was monitored by HPLC. After 6 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was triturated with diethyl ether (2 mL) and the precipitate collected by filtration and washed with diethyl ether (10 mL) and dried on the pump to afford 7-bromo-3-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid 4-fluoro-benzylamide (24 mg, 92%) as a yellow brown solid.

Workup

  1. temperatureto reflux
  2. customReaction progress
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with diethyl ether (2 mL)
  5. filtrationthe precipitate collected by filtration
  6. washwashed with diethyl ether (10 mL)
  7. customdried on the pump

Sources & evidence

ORD record
ord-d5fe4d81f1334424a21ba4d73733fe76
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

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