Triethylamine → 3-((Pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 454023Notes

Reaction equation

HRID 454023 reaction equation
Cl.CO[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1OCC1CCNCC1)[N:10]=[CH:9][N:8]([CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:7]2=[O:30].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].C(S(C)(=O)=O)=C>CO.C(Cl)Cl>[C:24]([O:23][CH2:22][N:8]1[C:7](=[O:30])[C:6]2[C:11](=[CH:12][CH:13]=[CH:4][CH:5]=2)[N:10]=[CH:9]1)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 19354Methyl vinyl sulfoneHCID 220306726-Methoxy-7-((piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one hydrochloride

Product 1

HCID 206891733-((Pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 105.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-7-((piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one hydrochloride (0.88 g, 2 mmol) and triethylamine (0.3 ml, 2.1 mmol) in methanol (10 ml) and methylene chloride (10 ml) was added potassium carbonate (280 mg, 2 mmol) and methyl vinyl sulfone (0.4 ml, 2.1 mmol). After stirring for 2 hours at ambient temperature, the volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4) and evaporated to give 6-methoxy-7-41-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (0.55 g, 54%).

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-8fad087c91bc4127b476835a6a537c2a
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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