Hydrochloric Acid → 6-Methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 634700Notes

Reaction equation

HRID 634700 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][N:7]=[C:6]2[O:21]C1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][NH:7][C:6]2=[O:21]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 216992756-Methoxy-4-phenoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline

Product 1

HCID 1354756166-Methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-oneYield 107%

Conditions

Temperature
90 °C

Procedure

A mixture of 6-methoxy-4-phenoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline (565 mg, 1.55 mmol) and 2M hydrochloric acid (5 ml) was heated at 90° C. for 90 minutes and allowed to cool. The solution was neutralised with aqueous sodium hydrogen carbonate, and the water removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol/ammonia (100/8/1) to give 6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (480 mg). This material was used without further characterisation.

Workup

  1. temperatureto cool
  2. customthe water removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol/ammonia (100/8/1)

Sources & evidence

ORD record
ord-6ed0625ebf8149eca2580ce134db39c3
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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