Potassium Carbonate → HCID 11463573, compound

HRID 634692Notes

Reaction equation

HRID 634692 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:17][CH:18]=[N:19]2)=[CH:14][C:13]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:30][O:29][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:12]=1[O:11][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[N:19]=[CH:18][N:17]=[C:16]2[O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 1354961377-Hydroxy-6-methoxy-4-phenoxyquinazoline

Product 1

HCID 11463573HCID 11463573, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

4-(3-Chloropropyl)morpholine (0.9 g, 4.5 mmol), (J. Am- Chem. Soc. 1945, 67, 736, 174 mg, 1.06 mmol), was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (1.0 g, 3.7 mmol), potassium carbonate (2.6 g, 18.8 mmol) in DMF (30 ml). The mixture was heated at 110° C. for 4 hours and then allowed to cool. The solids were removed by filtration, and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol, (96/4) to give 6-methoxy-7-(3-morpholinopropoxy)-4-phenoxyquinazoline (1.0 g, 68%).

Workup

  1. temperatureto cool
  2. customThe solids were removed by filtration
  3. customthe volatiles were removed from the filtrate by evaporation
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol, (96/4)

Sources & evidence

ORD record
ord-d2b117a74e494ee5afbfacc928d255cf
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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