Potassium Carbonate → HCID 22030816, compound

HRID 454037Notes

Reaction equation

HRID 454037 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:35])[CH:29]=[C:30]([CH3:34])[O:31]2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:5]=[CH:4][N:3]=[C:2]2[O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:35])[CH:29]=[C:30]([CH3:34])[O:31]2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 53553097-hydroxy-2-methyl-4H-1-benzopyran-4-oneHCID 117822304-Chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

Product 1

HCID 22030816HCID 22030816, compoundYield 92.1%

Conditions

Temperature
100 °C

Procedure

A suspension of 4-chloro-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (130 mg, 0.4 mmol), (prepared as described for the starting material in Example 10), 7-hydroxy-2-methylchromone (88 mg, 0.5 mmol), (Bull Soc. Chim. Fr. 1995, 132, 233), and potassium carbonate (83 mg, 0.6 mmol) was heated at 100° C. for 1.5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4), and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 6-methoxy-4-(2-methyl-4-oxo-4H-chromen-7-yloxy)-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (170 mg, 92%).

Workup

  1. custom(prepared
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. customThe residue was triturated with ether
  8. filtrationcollected by filtration
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-45d56de9b9f24212ba478dbb82dab185
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

Loading…