Diisopropylethylamine → 4-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1993401

Reaktionsgleichung

Cl[C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C(N(C(C)C)C(C)C)C.[C:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C(O)(CC)C>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=2)[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of 6-chloro-3H-pyrimidin-4-one (˜0.23 mol) in sec-butanol (525 mL) was added ethyldiisopropylamine (49.7 mL, 0.3 mol) and BOC-piperazine (available from Aldrich; 55.9 g, 0.3 mol). The reaction was stirred at 80° C. for 8 hours, and then allowed to cool to room temperature. The crude reaction mixture was filtered, and washed with sec-butanol to give 4-(6-oxo-1,6-dihydro-pyrimidin-4-yl) -piperazine-1-carboxylic acid tert-butyl ester (47.8 g, 74%) LCMS Purity=100% (Rt=1.42). 1H NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 5.34 (s, 1H), 3.56-3.46 (m, 4H), 3.46-3.38 (m, 4H), 1.38 (s, 9H).

Aufarbeitung

temperatureto cool to room temperature
customThe crude reaction mixture
filtrationwas filtered
washwashed with sec-butanol

Quellen und Nachweise

ORD-Eintrag: ord-2f222982204644f79249ebff68ab0e53
Quelldatensatz: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07652013B2

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