Ethylamine → 2-Ethylamino-4-(4-fluoro-2-methylphenyl)-8-(2,6-difluorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2357283

Reaktionsgleichung

Reaktionsgleichung von HRID 2357283
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[CH2:32]([NH2:34])[CH3:33]>C1COCC1>[CH2:32]([NH:34][C:16]1[N:17]=[C:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[CH3:26])[C:13]2[CH:12]=[CH:11][C:10](=[O:31])[N:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[C:14]=2[N:15]=1)[CH3:33]

Komponenten

4

Edukt 2

HCID 6341EthylamineHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Produkt 1

HCID 596396502-Ethylamino-4-(4-fluoro-2-methylphenyl)-8-(2,6-difluorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of Example 48 (200 mg, 0.45 mmol) was combined and stirred with 5 mL of a 2M solution of ethylamine in THF. After 5 min the solvents were removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography with 0-2% EtOAc/CH2Cl2 followed by recrystallization from CH2Cl2/hexane gave the product as a white-crystalline solid. mp 195-196°, LC MS m/z=411 (MH+). Retention time=2.4 min.

Aufarbeitung

  1. customAfter 5 min the solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhyd Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customFlash chromatography with 0-2% EtOAc/CH2Cl2 followed by recrystallization from CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d46edf5ac90a4b4db52e8bd0cd247999
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759486B2

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