2-Methoxyethylamine → HCID 21260353, compound

HRID 634750Notes

Reaction equation

HRID 634750 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].[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>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][NH:28][CH2:27][CH2:26][O:25][CH3:24])[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 80182-MethoxyethylamineHCID 212603117-(2-Bromoethoxy)-6-methoxy4-phenoxyquinazoline

Product 1

HCID 21260353HCID 21260353, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-(2-bromoethoxy)-6-methoxy-4-phenoxyquinazoline (1.1 g, 2.9 mmol), (prepared as described for the starting material in Example 22), in 2-methoxyethylamine (8 ml) was stirred at ambient temperature for 4 hours. The mixture was diluted with water and extracted with methylene chloride (5×25 ml). The combined extracts were washed with brine and passed through phase separating paper. The solvent was removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol/aqueous ammonia (100/8/1) to give 6-methoxy-4-phenoxy-7-(2-(2-methoxyethylamino)ethoxy)quinazoline (760 mg, 70%) as a white solid.

Workup

  1. custom(prepared
  2. extractionextracted with methylene chloride (5×25 ml)
  3. washThe combined extracts were washed with brine
  4. customseparating paper
  5. customThe solvent was removed by evaporation
  6. customthe residue purified by column chromatography
  7. washeluting with methylene chloride/methanol/aqueous ammonia (100/8/1)

Sources & evidence

ORD record
ord-91a57998025c4cc7ae296896f34f0f79
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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