Acetic Acid → 7-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 454228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454228
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[N:15]([CH2:20][O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:16]=[N:17]3)=[CH:12][C:11]=2[O:29][CH3:30])[CH2:3][CH2:2]1.C=O.[C:33](O)(=O)C.C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:33][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:28])[N:15]([CH2:20][O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:24])[CH3:25])[CH:16]=[N:17]3)=[CH:12][C:11]=2[O:29][CH3:30])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 117324937-(2-(Piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneHCID 131724855Sodium borohydride triacetate

Produkt 1

HCID 111128387-(2-(1-Methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-(2-(piperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (6 g, 14.4 mmol) in methanol (30 ml) and methylene chloride (60 ml) was added 37% aqueous formaldehyde (2.2 ml; 28.9 mmol) followed by acetic acid (990 μl; 17.3 mmol). Sodium borohydride triacetate (4.6 g, 21.6 mmol) was added in portions. After stirring for 1 hour at ambient temperature, the volatiles were removed under vacuum and the residue was partitioned between water (50 ml) and methylene chloride (50 ml). The pH of the aqueous layer was adjusted to 7, washed with water, brine, dried (MgSO4) and evaporated. The solid was triturated with ether, filtered, washed with ether and dried under vacuum to give 7-(2-(1-methylpiperidin-4-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (4.2 g, 68%).

Aufarbeitung

  1. customthe volatiles were removed under vacuum
  2. customthe residue was partitioned between water (50 ml) and methylene chloride (50 ml)
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe solid was triturated with ether
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-86a203898e0b4a45aa2fd97ee024a6ff
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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