Thiomorpholine → HCID 21260335, compound

HRID 634747Notes

Reaction equation

HRID 634747 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:22][CH3:23].[NH:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1>O>[CH3:23][O:22][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:3][CH2:2][N:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1)[N:12]=[CH:11][N:10]=[C:9]2[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 212603117-(2-Bromoethoxy)-6-methoxy4-phenoxyquinazoline

Product 1

HCID 21260335HCID 21260335, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2-Dibromoethane (19.2 ml, 286 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (6.0 g, 22 mmol), (prepared as described for the starting material in Example 16), and potassium carbonate (14.4 g, 107 mmol) in DMF. The mixture was stirred at 85° C. for 2.5 hours, allowed to cool and insoluble material was removed by filtration. The solvent was removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (93/7). The product was trituated with ethyl acetate to give 7-(2-bromoethoxy)-6-methoxy-4-phenoxyquinazoline (5.3 g, 63%). A mixture of 7-(2-bromoethoxy)-6-methoxy-4-phenoxyquinazoline (2.0 g, 5.3 mmol) in thiomorpholine (15 ml) was stirred at ambient temperature for 5 hours. The mixture was diluted with water and the resulting precipitate collected by filtration. The solid product was dissolved in methylene chloride, washed with brine and passed through phase separating paper. The solvent was removed by evaporation to give 6-methoxy-4-phenoxy-7-(2-thiomorpholinoethoxy)quinazoline (2.0 g, 94%) as a pale yellow solid.

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. dissolutionThe solid product was dissolved in methylene chloride
  3. washwashed with brine
  4. customseparating paper
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-718a598a04f8461eaca68277b3bcadc0
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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