Methyl iodide → N-[2,4-Dichloro-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide

HRID 270708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270708
[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[NH:18][C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[NH:22][C:23](=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.[H-].[Na+].I[CH3:38]>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]2[C:19](=[O:20])[N:18]([CH3:38])[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[NH:22][C:23](=[O:34])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59833903N-[2,4-Dichloro-3-(2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide

Produkt 1

HCID 59833840N-[2,4-Dichloro-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-[2,4-dichloro-3-(2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide (1.14 g, 2.17 mmol) in DMF (35 mL) is slowly added NaH (117.2 mg, 60%, 2.93 mmol) with stirring for 30 minutes a 0° C. Iodomethane (369 mg, 2.60 mmol) is added to above solution with stirring for 40 minutes at 0° C. The solvents are evaporated and diluted with EtOAc and washed with saturated K2CO3, brine and water. The organic layer is dried, filtered and concentrated to give crude product, which is purified by flash silica gel column, eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH(NH3, 2N)(93/7), to give the title intermediate as a solid (1.14 g, 98.0%).

Aufarbeitung

  1. stirringwith stirring for 40 minutes at 0° C
  2. customThe solvents are evaporated
  3. additiondiluted with EtOAc
  4. washwashed with saturated K2CO3, brine and water
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customis purified by flash silica gel column
  10. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH(NH3, 2N)(93/7)

Quellen und Nachweise

ORD-Eintrag
ord-98e79c30629d4c1199e1ad98876da7f4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449582B2

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