Ethanol → 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine

HRID 220084

Reaktionsgleichung

[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([NH:9][NH2:10])[CH:4]=1.N=[C:12]([CH3:16])[CH2:13][C:14]#[N:15].C(O)C>C(OCC)(=O)C>[CH3:16][C:12]1[CH:13]=[C:14]([NH2:15])[N:9]([C:5]2[CH:4]=[C:3]([S:2][CH3:1])[N:8]=[CH:7][N:6]=2)[N:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

The mixture of (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine (1.0 g, 6.4 mmol), 3-Imino-butyronitrile (1.1 g, 12.8 mmol), and ethanol (30 mL) is heated to 85° C. for overnight. The reaction mixture is then cooled to room temperature, condensed, and treated with 75 mL ethyl acetate. The reaction mixture is partitioned between ethyl acetate and aqueous layer. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80% to afford 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.72 (s, 1H), 7.53 (s, 1H), 6.90 (s, 1H), 5.26 (s, 1H), 2.57 (s, 3H), 2.08 (s, 3H); MS m/z 222.07 (M+1).

Aufarbeitung

temperatureThe reaction mixture is then cooled to room temperature
customcondensed
customThe reaction mixture is partitioned between ethyl acetate and aqueous layer
dry with materialThe organic layer is dried over Na2SO4
concentrationconcentrated
customThe crude product is purified by ISCO chromatography
washeluting with ethyl acetate in hexanes from 10% to 80%

Quellen und Nachweise

ORD-Eintrag: ord-e8f9c9326c874781be6fe58dad94815f
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08202876B2

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