4-Hydroxymethylpyridine → 7-(4-Pyridylmethoxy)-3,4-dihydroquinazolin-4-one

HRID 279543

Reaction equation

[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.F[C:12]1[CH:21]=[C:20]2[C:15]([C:16](=[O:22])[NH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1>C1COCC1>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][O:3][C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:22])[NH:17][CH:18]=[N:19]3)=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium hydride (0.72 g of a 60% suspension in mineral oil, 18 mmol) was added to a solution of 4-hydroxymethylpyridine (4 g, 36 mmol) in THF (30 ml) and the mixture heated at reflux for 15 minutes. 7-Fluoro-3,4-dihydroquinazolin-4-one (1 g, 6 mmol), (J. Chem. Soc. section B 1967, 449), was added, the THF was removed by evaporation, and the mixture was heated at 120° C. for 30 minutes. The mixture was allowed to cool, diluted with water (40 ml) and was adjusted to pH8 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, then ether and dried under vacuum to give 7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (1.12 g, 71%).

Workup

temperaturethe mixture heated
temperatureat reflux for 15 minutes
customthe THF was removed by evaporation
temperatureto cool
additiondiluted with water (40 ml)
filtrationThe resulting precipitate was collected by filtration
washwashed with water
dry with materialether and dried under vacuum

Sources & evidence

ORD record: ord-c6c09be9b5234091846e359d2e745dfc
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362336B1

Linked notes

Loading…