Ammonia → 7-((6-Chloro-2-oxo-1,2-dihydropyrid-4-yl)methoxy)-6-methoxy-3,4-dihydroquinazolin-4-one

HRID 279605Notes

Reaction equation

HRID 279605 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14]([O:20]C4C=CC=CC=4)=[N:15][CH:16]=[N:17]3)=[CH:12][C:11]=2[O:27][CH3:28])[CH:5]=[C:4]([O:29]C)[N:3]=1.N>Cl>[Cl:1][C:2]1[NH:3][C:4](=[O:29])[CH:5]=[C:6]([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:20])[NH:15][CH:16]=[N:17]3)=[CH:12][C:11]=2[O:27][CH3:28])[CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 226248857-((2-Chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy4-phenoxyquinazoline

Product 1

HCID 1360614627-((6-Chloro-2-oxo-1,2-dihydropyrid-4-yl)methoxy)-6-methoxy-3,4-dihydroquinazolin-4-oneYield 60%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 7-((2-chloro-6-methoxy-4-pyridyl)methoxy)-6-methoxy-4-phenoxyquinazoline (400 mg, 0.95 mmol) and 2M hydrochloric acid (20 ml) was heated at reflux for 3 hours. The mixture was allowed to cool and adjusted to pH6-7 with aqueous ammonia solution. The resulting precipitate was collected by filtration washed with water and dried to give crude 7-((6-chloro-2-oxo-1,2-dihydropyrid-4-yl)methoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (190 mg, 60%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-996547c495c2481e950701fbf37c78cc
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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