4,6-Dichloro-2-(methylthio)pyrimidine → Ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate

HRID 469273

Reaktionsgleichung

Reaktionsgleichung von HRID 469273
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.O>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 235927Ethyl 6-AminonicotinateHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 86679315Ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloro-2-(methylthio)pyrimidine (1 g), ethyl 6-aminonicotinate (0.85 g) and NaHMDS (10.3 mL, 1M in THF) in THF (50 mL) was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted with EtOAc (2×150 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4 and concentrated to give ethyl 6-(6-chloro-2-(methylthio)pyrimidin-4-ylamino)nicotinate which was used as was.

Aufarbeitung

  1. extractionextracted with EtOAc (2×150 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-93d8f17e7b9343648392cf65a432290e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629150B2

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