Ethyl orthoformate → HCID 135485944, compound

HRID 1059629Notes

Reaction equation

HRID 1059629 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:12](OCC)(OCC)OCC>>[F:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:5])[NH:6][CH:12]=[N:1][C:2]=2[N:10]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 131513852-Amino-6-fluoronicotinamide

Product 1

HCID 135485944HCID 135485944, compoundYield 96%

Procedure

A suspension of 2-amino-6-fluoronicotinamide (0.74 g, 4.77 mmol) in triethyl orthoformate (25 mL) is heated at reflux for 8 h. After cooling to room temperature the precipitate is filtered off and washed well with petroleum ether to give 7-fluoropyrido[2,3-d]pyrimid-4(3H)-one (0.76 g, 96%). 1H NMR (DMSO) δ 12.75 (1H, brs), 8.66 (1H, dd, J=10.4, 8.4 Hz), 8.38 (1H, s), 7.33 (1H, dd, J=8.4, 2.6 Hz).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 8 h
  3. filtrationis filtered off
  4. washwashed well with petroleum ether

Sources & evidence

ORD record
ord-97079072cb6d4202ac7dba1b902271e9
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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