m-Toluidine → Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 711419

Reaktionsgleichung

Reaktionsgleichung von HRID 711419
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:4]([CH3:13])[N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1.C(N(C(C)C)C(C)C)C>CC#N.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:13])[C:5]([C:9]([O:11][CH3:12])=[O:10])=[C:6]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[N:7]=1

Komponenten

6

Edukt 3

HCID 7934m-ToluidineHCID 81531DiisopropylethylamineHCID 57531614Methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate

Produkt 1

HCID 58317549Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (940 mg, 4.25 mmol), m-toluidine (0.461 mL, 4.25 mmol) and N-ethyldiisopropylamine (1.481 mL, 8.51 mmol) in CH3CN (30 mL) was heated under reflux for 3 h. The mixture was diluted with EtOAc, and was washed with brine and water. The organic extract was dried and concentrated under reduced pressure to give the title compound as a light yellow solid (1.2 g, 97%). [M+H] calc'd for C14H14N3ClO2, 292. found, 292.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. washwas washed with brine and water
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce593d69bc9c4575a2472c690a7fcd7f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181255B2

Verknüpfte Notizen

Wird geladen…