Sodium Carbonate → HCID 135456619, compound

HRID 2287684Notes

Reaction equation

HRID 2287684 reaction equation
N[C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1.N([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[H+].[B-](F)(F)(F)[F:25]>>[F:25][C:2]1[N:11]=[CH:10][C:9]2[C:8](=[O:12])[NH:7][CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 23668193Sodium NitriteHCID 1354805187-Aminopyrido[4,3-d]pyrimidin-4(3H)-one

Product 1

HCID 135456619HCID 135456619, compoundYield 47%

Conditions

Temperature
20 °C

Procedure

A solution of 7-amino-4-oxo-3H-pyrido[4,3-d]pyrimidine (1.00 g, 6.17 mmol) in 60% HBF4 (25 mL) at 0° C. is treated with solid NaNO2 (0.85 g, 12.3 mmol, added in portions over 2 h), and is then stirred at 0° C. for a further 1 h and at 20° C. for 30 min. The resulting mixture is ice-cooled, neutralized with saturated aqueous Na2CO3, and extracted with EtOAc (4×100 mL). The extract is washed with water, then filtered through silica gel (EtOAc) to give 7-fluoro-4-oxo-3H-pyrido[4,3-d]pyrimidine (0.48 g, 47%) as a cream solid. 1H NMR (DMSO) δ 12.69 (1H, brs), 9.01 (1H, s), 8.31 (1H, s), 7.34 (1H, s)

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (4×100 mL)
  3. washThe extract is washed with water
  4. filtrationfiltered through silica gel (EtOAc)

Sources & evidence

ORD record
ord-f34f9ef089f2415ca9f8ce5ebf6eeb4a
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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