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

HRID 1420938Notes

Reaction equation

HRID 1420938 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

5

Reactant 3

HCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 1353984967-Fluoroquinazolin-4(3H)-one

Product 1

HCID 1356711817-(4-Pyridylmethoxy)-3,4-dihydroquinazolin-4-oneYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-dihydroquinazolin4-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

  1. temperaturethe mixture heated
  2. temperatureat reflux for 15 minutes
  3. customthe THF was removed by evaporation
  4. temperatureto cool
  5. additiondiluted with water (40 ml)
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-4ffd32aa97aa47ce8a4d4db6163a0cc6
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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