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

HRID 1597221Notes

Reaction equation

HRID 1597221 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 98.1%

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 (440 mg, 98%yield). 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-eca221433a7c49d39b0536a2ba44d2da
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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