Ammonia → 7-methoxy-5-((1-methylpiperidin-4-yl)oxy)quinazolin-4(3H)-one

HRID 749189Notes

Reaction equation

HRID 749189 reaction equation
N.C(OC[N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([O:29][CH3:30])=[CH:16][C:17]=2[O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[N:12]=[CH:11]1)(=O)C(C)(C)C>CO>[CH3:30][O:29][C:15]1[CH:14]=[C:13]2[C:18]([C:19](=[O:20])[NH:10][CH:11]=[N:12]2)=[C:17]([O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[CH:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 119739027-methoxy-5-(N-methylpiperidin-4-yloxy)-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 1355106997-methoxy-5-((1-methylpiperidin-4-yl)oxy)quinazolin-4(3H)-oneYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.0 N ammonia in methanol (25 ml) was added to (7-methoxy-5-((1-methylpiperidin-4-yl)oxy)-4-oxoquinazolin-3(4H)-yl)methyl pivalate (370 mg, 0.92 mmol) and the solution stirred at ambient temperature for 18 hours. The reaction mixture was concentrated in vacuo to give an oil which was triturated with diethyl ether to give an orange solid which was collected by suction filtration and dried in vacuo to yield 7-methoxy-5-((1-methylpiperidin-4-yl)oxy)quinazolin-4(3H)-one (200 mg, 75% yield):

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give an oil which
  3. customwas triturated with diethyl ether
  4. customto give an orange solid which
  5. filtrationwas collected by suction filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cdd18f06ff2444b48d0bfc621990b6d3
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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