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

HRID 19624
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19624
[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
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Komponenten

5

Edukt 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 593465585,6,7,8-Tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amine

Produkt 1

HCID 593464736-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-N-phenylpyrido[4,3-d]pyrimidin-4-amineAusbeute 25,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67000103
dioxane N,N-dimethylacetamide
Lösungsmittel

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

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a brown residue
  8. 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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