Ethanol → 4-(4-{4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl}phenyl)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 908124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908124
[NH2:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]45[CH2:25][CH2:24][C:21]([C:26]([O:28]C)=[O:27])([CH2:22][CH2:23]4)[CH2:20][CH2:19]5)=[CH:14][CH:13]=3)[C:8]([CH3:31])([CH3:30])[O:7][C:6]=2[N:5]=[CH:4][N:3]=1.[OH-].[Na+].CCO>CO>[NH2:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]45[CH2:23][CH2:22][C:21]([C:26]([OH:28])=[O:27])([CH2:20][CH2:19]4)[CH2:24][CH2:25]5)=[CH:16][CH:17]=3)[C:8]([CH3:31])([CH3:30])[O:7][C:6]=2[N:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 25258106methyl 4-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]bicyclo[2.2.2]octane-1-carboxylate2×

Produkt 1

HCID 250164264-(4-{4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl}phenyl)bicyclo[2.2.2]octane-1-carboxylic acidAusbeute 724,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-[4-(4-amino-7,7-dimethyl-7H-pyrimido[4,5-b][1,4]oxazin-6-yl)phenyl]bicyclo[2.2.2]octane-1-carboxylate (Intermediate 27; 140 mg, 0.33 mmol) in MeOH (10 mL) was added 2M NaOH (0.82 mL, 1.66 mmol). The reaction mixture was allowed to stir at ambient temperature overnight and then after the addition of EtOH (˜5 mL) and 1M NaOH (2 mL) the reaction mixture was heated to 50° C. for 5.5 hrs. The organic solvent was removed by evaporation under reduced pressure and the residue was acidified to pH 2 with 2M HCl. EtOAc was added and the suspension was filtered and dried to provide the title compound (97 mg, 2.39 mmol, 72%); 1H NMR δ 1.60 (s, 6H), 1.82 (s, 12H), 6.97 (s, 1H), 7.40 (d, 2H), 7.65 (d, 2H), 7.95 (s, 1H), NH2 not seen; MS m/e MH+ 407.

Aufarbeitung

  1. temperaturewas heated to 50° C. for 5.5 hrs
  2. customThe organic solvent was removed by evaporation under reduced pressure
  3. additionEtOAc was added
  4. filtrationthe suspension was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-741dfe5e71174cd5a48833074dae8505
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017603B2

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