Sodium Iodide → 7-(3-Chloropyridin-2-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971220
Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[I-].[Na+].I>C(#N)C>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:24][C:23]4[CH:25]=[CH:26][C:20]([F:19])=[CH:21][CH:22]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 97314-FluoroanilineHCID 24841Hydrogen iodideHCID 590214784-Chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Produkt 1

HCID 120043457-(3-Chloropyridin-2-yl)-N-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

4-Chloro-7-(3-chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine (100 mg, 0.35 mmol) was dissolved in acetonitrile (2 mL). To the mixture was added 4-flouroaniline (0.067 mL, 0.71 mmol), sodium iodide (80 mg, 0.53 mmol) and HI (47%, 0.2 mL). The mixture was heated in a sealed tube at 130° C. for 10 minutes in a Personal Chemistry Microwave (Smith Creator). The solvent was removed under vacuum and the resulting orange residue dissolved in ethyl acetate and washed with saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient to give the product as an off white solid (53 mg).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting orange residue dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography over silica gel using a 0-100% ethyl acetate-hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-042d79184818475286e837391415b976
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312330B2

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