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2-Pyridinemethanamine → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 34

HRID 3189
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3189
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=2[CH:10]=1.[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 195092-PyridinemethanamineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 53278812-aminopyrido[2,3-d]pyrimidin-7(8H)-one 34Ausbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 1.08 g (10.0 mmol) of 2-(aminomethyl)pyridine and 0.5 mL of dimethylformamide was heated with stirring in a 130° C. oil bath. After 2 minutes, solution was complete. After 2 hours, the excess amine and dimethylformamide were evaporated at reduced pressure. Ether (5 mL) was added to the residue. Crystals immediately developed. Water (5 mL) was added, and the entire mixture was filtered. The cake was washed 5 mL of ether, 5 mL of water, and then dried; wt 0.164 g. Recrystallization from ethyl acetate gave 0.075 g of pure product; mp 198°-201° C.

Aufarbeitung

  1. temperaturewas heated
  2. waitAfter 2 hours
  3. customthe excess amine and dimethylformamide were evaporated at reduced pressure
  4. additionEther (5 mL) was added to the residue
  5. additionWater (5 mL) was added
  6. filtrationthe entire mixture was filtered
  7. washThe cake was washed 5 mL of ether, 5 mL of water
  8. customdried
  9. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4065ebd450dd42b9b396a7e3dbade98c
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05733914

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