Water → 6-fluoropyrido[3,4-d]pyrimidin-4-ol

HRID 428364

Reaction equation

HRID 428364 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.O.C(O)(=O)C.[CH:17](N)=[NH:18]>COCCO>[F:8][C:5]1[N:6]=[CH:7][C:2]2[N:1]=[CH:17][NH:18][C:9](=[O:11])[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 160693Formamidine acetateHCID 27625115-Amino-2-fluoroisonicotinic acid

Product 1

HCID 1354173706-fluoropyrido[3,4-d]pyrimidin-4-ol

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A suspension of 39.0 g (246 mmol) of 5-amino-2-fluoropyridine-4-carboxylic acid hydrated with 0.15 equivalents of water, 52.01 g (500 mmol) of formamidine acetate, and 500 mL of 2-methoxyethanol was heated at reflux for 6 hours, then concentrated to a solid. The solids were treated carefully with 100 mL of 10% aqueous sodium bicarbonate while maintaining vigorous stirring. The resultant suspension was filtered, and the collected brown solids were washed well with water, then dried over P2O5 to afford 31.3 g (77%,) of product that was used directly in the next reaction. Recrystallization of a small sample from methanol gave product of mp 287° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationconcentrated to a solid
  4. additionThe solids were treated carefully with 100 mL of 10% aqueous sodium bicarbonate
  5. temperaturewhile maintaining vigorous stirring
  6. filtrationThe resultant suspension was filtered
  7. washthe collected brown solids were washed well with water
  8. dry with materialdried over P2O5
  9. customto afford 31.3 g (77%,) of product that
  10. customwas used directly in the next reaction
  11. customRecrystallization of a small sample from methanol
  12. customgave product of mp 287° C. (dec)

Sources & evidence

ORD record
ord-1186a5a9cee0407face6210372eeaa37
Source dataset
uspto-grants-2001_11
Patent number
US06313292B1

Linked notes

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