tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(3-methyl-4-oxo-3,4-dihydropteridin-6-yl)piperazine-1-carboxylate

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Reaktionsgleichung

[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:15]1[N:16]=[C:17]2[C:22](=[N:23][CH:24]=1)[N:21]=[CH:20][N:19]([CH3:25])[C:18]2=[O:26]>COCCO>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:15]2[N:16]=[C:17]3[C:22](=[N:23][CH:24]=2)[N:21]=[CH:20][N:19]([CH3:25])[C:18]3=[O:26])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a stirred solution of 1-Boc-piperazine (18.9 g, 101.4 mmol) in 2-methoxyethanol (100 mL) was added 6-bromo-3-methyl-3H-pteridin-4-one (11.6 g, 48 mmol; see Example 16 (c) above) and the resulting suspension was heated for 3 hours at 100° C. The reaction was then cooled in an ice-water bath and the precipitate that formed was collected, washed with cold MeOH, and dried to afford 4-(3-methyl-4-oxo-3,4-dihydro-pteridin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (15.2 g, 92%). 1H NMR (300 MHz, CDCl3) δ1.48 (s, 9H), 3.57-3.61 (m, 4H), 3.62 (s, 3H),3.78-3.82 (m, 4H), 8.07 (s, 1H), 8.56 (s, 1 H); 13C NMR (100 MHz, CDCl3) δ28.38, 34.42, 44.40, 80.38, 130.64, 137.93, 145.53, 147.04, 152.91, 154.61, 160.89.

Aufarbeitung

temperatureThe reaction was then cooled in an ice-water bath
customthe precipitate that formed
customwas collected
washwashed with cold MeOH
customdried

Quellen und Nachweise

ORD-Eintrag: ord-ce877bc04c6a4cedb4465f1a45e2618c
Quelldatensatz: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07674791B2

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