Diisopropylethylamine → Ethyl 2-chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylate

HRID 559001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559001
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([NH2:26])[CH:18]=[CH:19][C:20]=1[C:21]1[N:22]=[CH:23][S:24][CH:25]=1.CCN(C(C)C)C(C)C>CC#N>[Cl:1][C:2]1[N:7]=[C:6]([NH:26][C:17]2[CH:18]=[CH:19][C:20]([C:21]3[N:22]=[CH:23][S:24][CH:25]=3)=[C:15]([F:14])[CH:16]=2)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 574718803-Fluoro-4-(thiazol-4-yl)benzenamine

Produkt 1

HCID 57471881Ethyl 2-chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylateAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (165 mg, 0.746 mmol) and 3-fluoro-4-(thiazol-4-yl)benzenamine (145 mg, 0.747 mmol) in CH3CN (5 mL) at room temperature, DIEA (0.260 mL, 1.49 mmol) was added. The mixture was stirred at room temperature overnight, during which time solids precipitated out. The precipitate was collected, dried on vacuum to give ethyl 2-chloro-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxylate as a solid (186 mg). MS 379.3 and 381.3 (M+H, Cl pattern)

Aufarbeitung

  1. customprecipitated out
  2. customThe precipitate was collected
  3. customdried on vacuum

Quellen und Nachweise

ORD-Eintrag
ord-911c51f4e0ac41e28385386710529678
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063058B2

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