Potassium Carbonate → HCID 21114608, compound

HRID 749201Notes

Reaction equation

HRID 749201 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22].Br[CH2:24][CH2:25][CH2:26][OH:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 21114610HCID 21114610, compound

Product 1

HCID 21114608HCID 21114608, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 2-[7-hydroxy-6-methoxy-4-oxo-3(4H)-quinazolinyl]-acetate (100 g, 0.327 mol), 3-bromopropanol (49.3 g, 0.355 mol) and potassium carbonate (133 g, 0.967 mol) in dimethylformamide (500 ml) was stirred at 80° C. for 20 hours. The reaction was cooled and concentrated to quarter volume in vacuo. The residue was poured into ice/water (1500 ml) and the resulting solid collected by suction filtration. Purification by crystallisation from ethanol, yielded crude tert-butyl 2-[7-(3-hydroxypropoxy)-6-methoxy-4-oxo-3(4H)-quinazolinyl]acetate (33.8 g, 41% yield) as a beige solid:

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated to quarter volume in vacuo
  3. additionThe residue was poured into ice/water (1500 ml)
  4. filtrationthe resulting solid collected by suction filtration
  5. customPurification
  6. customby crystallisation from ethanol

Sources & evidence

ORD record
ord-97fefaeb2e704d6e87529f497d2070aa
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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