Ammonia → 6-Methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4(3H)-one

HRID 577372Notes

Reaction equation

HRID 577372 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][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:10]=[CH:9][N:8](COC(=O)C(C)(C)C)[C:7]2=[O:31]>CO.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][CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[N:10]=[CH:9][NH:8][C:7]2=[O:31]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 109934456-Methoxy-7-(1-methylpiperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 1354703756-Methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4(3H)-oneYield 90.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A saturated solution of ammonia in methanol (14 ml) was added to a solution of 6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.38 g, 3.3 mmol) in methanol (5 ml). After stirring for 20 hours at ambient temperature, the suspension was diluted with methylene chloride (10 ml). The solution was filtered. The filtrate was evaporated under vacuum and the residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)-3,4-dihydroquinazolin-4-one (910 mg, 83%).

Workup

  1. filtrationThe solution was filtered
  2. customThe filtrate was evaporated under vacuum
  3. customthe residue was triturated with ether
  4. filtrationcollected by filtration
  5. washwashed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c4de8abe0e544983b32854d83c2506de
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

Loading…