1,4-Dioxane → 5,6,7,8-Tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 241840

Reaktionsgleichung

[N:1]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]=2[C:4](=[O:11])[NH:3][CH:2]=1.Cl[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=1.O1CCOCC1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.CC(O)C.CN(C)C(=O)C>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([N:9]2[CH2:8][CH2:7][C:6]3[N:1]=[CH:2][NH:3][C:4](=[O:11])[C:5]=3[CH2:10]2)=[N:14][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

Into a 20 mL microwave tube was combined 5,6,7,8-tetrahydro-3H-pyrido[4,3-d]pyrimidin-4-one (0.280 g, 1.83 mmol), 2-chloro-5-methylpyridine (0.47 g, 3.7 mmol), 1,4-dioxane (2.5 mL), N,N-diisopropylethylamine (0.64 mL, 3.7 mmol) and N,N-dimethylacetamide (0.5 mL). The mixture was heated via microwave at 150° C. for 4 hours. The mixture was reduced in vacuo and taken up in chloroform:IPA (3:1) (50 mL). The organic phase was washed with sodium bicarbonate and brine (1×50 mL), dried over sodium sulfate, and reduced in vacuo. The residue was purified by flash chromatography on silica gel (0-10% methanol/methylene chloride) to give a bright yellow solid (0.215 g, 47.9%). MS: 243.3 [M+1]+.

Aufarbeitung

customInto a 20 mL microwave tube was combined
washThe organic phase was washed with sodium bicarbonate and brine (1×50 mL)
dry with materialdried over sodium sulfate
customThe residue was purified by flash chromatography on silica gel (0-10% methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag: ord-ee487f9731e740129df005f175727be1
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653091B2

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