Ethanol → 4-Ethoxy-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amine

HRID 1025522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025522
[NH2:1][C:2]1[N:3]=[C:4](SC)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Na].[CH2:22]([OH:24])[CH3:23]>>[NH2:1][C:2]1[N:3]=[C:4]([O:24][CH2:22][CH3:23])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 5360545SodiumHCID 249572632-Amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidine

Produkt 1

HCID 689211024-Ethoxy-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amineAusbeute 72 %

Versuchsvorschrift

To a solution of the 2-amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidine of example 8 (700 mg) in ethanol (20 ml) was added 276 mg sodium. The reaction mixture was refluxed for 5 hours and then cooled down. The solvents were evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of ethanol and dichloromethane, in a volume ratio gradually ranging from 3% to 5% ethanol, thus providing 490 mg of the pure title compound (72% yield), which was characterized by its mass spectrum as follows: MS (m/z): 285 ([M+H]+, 100).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. temperaturecooled down
  3. customThe solvents were evaporated in vacuo
  4. customthe crude residue was purified by silica gel flash chromatography
  5. additiona mixture of ethanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-91450939219f4c96991e3810a73a08c6
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729089B2

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