2,3-Dichloropyridine → 6-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine

HRID 19624

Reaktionsgleichung

[C:1]1([NH:7][C:8]2[C:9]3[CH2:17][NH:16][CH2:15][CH2:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.CN(C)C(=O)C>[Cl:25][C:24]1[C:19]([N:16]2[CH2:15][CH2:14][C:10]3[N:11]=[CH:12][N:13]=[C:8]([NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:9]=3[CH2:17]2)=[N:20][CH:21]=[CH:22][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

5,6,7,8-Tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine (500 mg, 2.2 mmol) was dissoled in a mixture of dioxane/N,N-dimethylacetamide (4:1) (2 mL). To the mixture was added 2,3-dichloropyridine (423 mg, 2.86 mmol) and N,N-diisopropylethylamine (0.38 mL, 2.2 mmol). The mixture was heated at 150° C. in a microwave (Emrys Optimizer model, Personal Chemistry) for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a brown residue. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an off-white powder (190 mg).

Aufarbeitung

customThe solvents were removed under vacuum
dissolutionthe residue was dissolved in ethyl acetate
washwashed with sat. NaHCO3 and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customto give a brown residue
customThe residue was purified

Quellen und Nachweise

ORD-Eintrag: ord-0254c620f8884a0a8f85c0b6c4abe0e9
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745451B2

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