Sodium hydride → HCID 21260333, compound

HRID 634712Notes

Reaction equation

HRID 634712 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:19][CH3:20].[H-].[Na+].C1(C)C=CC(S(O[CH2:33][CH2:34][O:35][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)(=O)=O)=CC=1>CN(C=O)C>[CH:36]1([O:35][CH2:34][CH2:33][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:19][CH3:20])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13187521HCID 13187521, compoundHCID 1354961377-Hydroxy-6-methoxy-4-phenoxyquinazoline

Product 1

HCID 21260333HCID 21260333, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

7-Hydroxy-6-methoxy-4-phenoxyquinazoline (1.11 g, 4.2 mmol), (prepared as described for the starting material in Example 16), in DMF (1 7 ml) was added to a suspension of sodium hydride (184 mg of a 60% suspension in oil, 4.6 mmol) in DMF (3 ml). The mixture was stirred until evolution of gas ceased, and then 2-cyclopentyloxyethyl 4-toluenesulphonate (1.25 g, 4.45mmol) in DMF (3 ml) was added dropwise. The mixture was stirred at ambient temperature for 30 minutes, then heated at 60° C. for 2 hours, and then at 80° C. for a further 4 hours before being allowed to cool. The mixture was poured onto ice and extracted with methylene chloride. The combined extracts were washed with brine, passed through phase separating paper and the solvent removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate. The purified product was triturated with isohexane to give 7-(2-cyclopentyloxyethoxy)-6-methoxy-4-phenoxyquinazoline (480 mg, 28%).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 minutes
  2. temperatureto cool
  3. additionThe mixture was poured onto ice
  4. extractionextracted with methylene chloride
  5. washThe combined extracts were washed with brine
  6. customseparating paper
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate
  10. customThe purified product was triturated with isohexane

Sources & evidence

ORD record
ord-673fa9ebaf31439385298f423d5e17c5
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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