O-Toluidine → 6-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946674

Reaktionsgleichung

Reaktionsgleichung von HRID 1946674
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1.[NH2:28][C:29]1[C:30]([CH3:35])=[CH:31][CH:32]=[CH:33][CH:34]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:9])[CH:3]=1

Komponenten

6

Edukt 4

HCID 7242O-ToluidineHCID 81531DiisopropylethylamineHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

Produkt 1

HCID 594470936-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride (26.76 g; 151 mmol), obtained as described above for Intermediate 7 step 1, in anhydrous DCM (270 ml) was treated dropwise over 25 minutes with a solution of o-toluidine (13.6 ml; 126.0 mmol) and DIEA (43.4 ml; 252 mmol) in anhydrous DCM (100 mL). At the end of addition, the reaction mixture was washed with water then brine, dried over MgSO4, filtered and dried under vacuum to afford the title compound used without further purification as a brown solid.

Aufarbeitung

  1. customobtained
  2. additionAt the end of addition
  3. washthe reaction mixture was washed with water
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cb24b151bebc49458ba5df50805742d7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399448B2

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