HCID 178526462, compound → HCID 178507326, compound

HRID 1696556Notes

Reaction equation

HRID 1696556 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([OH:14])=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([OH:14])=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 178526462HCID 178526462, compound

Product 1

HCID 178507326HCID 178507326, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-nitroquinazolin-4-ol (3.62 g, 18.9 mmol) with 10% Pd/C (0.25 g) in DMF (15 mL) was stirred under H2 (1 atm) for 18 h, then partially concentrated at elevated temperature, filtered warm through Celite® to remove catalyst and then concentrated to a brown solid. The solid was triturated with EtOAc (50 mL), filtered, dried, redissolved in DMF (25 mL), treated with 10% Pd/C (0.25 g) and stirred overnight under an H2 atmosphere. The mixture was filtered free of catalyst and the filtrate evaporated at reduced pressure to yield a brown solid which was triturated with EtOAc (50 mL) and filtered to yield 7-aminoquinazolin-4-ol (2.27 g, 74% yield). MS (ESI) m/e (M+H+) 162.3.

Workup

  1. concentrationpartially concentrated at elevated temperature
  2. filtrationfiltered
  3. temperaturewarm through Celite®
  4. customto remove catalyst
  5. concentrationconcentrated to a brown solid
  6. customThe solid was triturated with EtOAc (50 mL)
  7. filtrationfiltered
  8. customdried
  9. dissolutionredissolved in DMF (25 mL)
  10. additiontreated with 10% Pd/C (0.25 g)
  11. filtrationThe mixture was filtered free of catalyst
  12. customthe filtrate evaporated at reduced pressure
  13. customto yield a brown solid which
  14. customwas triturated with EtOAc (50 mL)
  15. filtrationfiltered

Sources & evidence

ORD record
ord-566f2854363f4e3f9420951c223812ec
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…