Ammonia → 6-Methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazolin-4(1H)-one

HRID 1791696Notes

Reaction equation

HRID 1791696 reaction equation
N.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[N:10]=[CH:9][N:8](COC(=O)C(C)(C)C)[C:7]2=[O:30]>C(O)C.C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[N:10]=[CH:9][NH:8][C:7]2=[O:30]

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 22030859HCID 22030859, compound

Product 1

HCID 1357422856-Methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazolin-4(1H)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Saturated methanolic ammonia (20 ml) was added to a solution of 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.26 g, 5.5 mmol) in a mixture of ethanol (40 ml) and methylene chloride (15 ml). The mixture was stirred for 24 hours at ambient temperature, and further methanolic ammonia (20 ml) was added. The mixture was stirred for a further 24 hours at ambient temperature and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, dried under vacuum to give 6-methoxy-7-(2-(2-methoxyethoxy)ethoxy)-3,4-dihydroquinazolin-4-one (975 mg, 78%).

Workup

  1. stirringThe mixture was stirred for a further 24 hours at ambient temperature
  2. customthe volatiles were removed by evaporation
  3. customThe residue was triturated with ether
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-784e8afcd41e42f19330f8334793a087
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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