Sodium Bicarbonate → HCID 135549385, compound

HRID 634751Notes

Reaction equation

HRID 634751 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][NH:16][CH2:17][CH2:18][O:19][CH3:20])[N:9]=[CH:8][N:7]=[C:6]2[O:21]C1C=CC=CC=1.C(=O)([O-])O.[Na+]>Cl>[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][NH:16][CH2:17][CH2:18][O:19][CH3:20])[N:9]=[CH:8][NH:7][C:6]2=[O:21]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 21260353HCID 21260353, compound

Product 1

HCID 135549385HCID 135549385, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-methoxy-4-phenoxy-7-(2-(2-methoxyethylamino)ethoxy)quinazoline (760 mg, 2 mmol) in 2M hydrochloric acid (5 ml) was heated at 90° C. for 1.5 hours. The mixture was allowed to cool and adjusted to pH7 with solid sodium hydrogen carbonate. The water was removed by evaporation and the residue extracted with methylene chloride/methanol/aqueous ammonia (100/8/1). The volatiles were removed from the extract by evaporation, the residue dissolved in methylene chloride, passed through phase separating paper and the solvent removed by evaporation to give 6-methoxy-7-(2-(2-methoxyethylamino)ethoxy)-3,4-dihydroquinazolin-4-one (600 mg, 99%) as a white solid.

Workup

  1. temperatureto cool
  2. customThe water was removed by evaporation
  3. extractionthe residue extracted with methylene chloride/methanol/aqueous ammonia (100/8/1)
  4. customThe volatiles were removed from the
  5. extractionextract by evaporation
  6. dissolutionthe residue dissolved in methylene chloride
  7. customseparating paper
  8. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-fe138c45382643ab8ec214b281373ede
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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