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

HRID 454023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454023
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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 206891733-((Pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneAusbeute 105,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8fad087c91bc4127b476835a6a537c2a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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