4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → Ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylate

HRID 533473

Reaktionsgleichung

Reaktionsgleichung von HRID 533473
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[C:15]1([C:21]2([NH2:24])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CC#N.CCOC(C)=O>[CH3:14][S:13][C:4]1[N:3]=[C:2]([NH:24][C:21]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:23][CH2:22]2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Komponenten

6

Edukt 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 1945491-Phenyl-cyclopropylamine

Produkt 1

HCID 58098733Ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylateAusbeute 104,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (550 mg, 2.36 mmol) and 1-phenylcyclopropanamine (420 mg, 3.16 mmol) in CH3CN (6 mL) at room temperature was added DIEA (0.5 mL, 2.60 mmol). The mixture was stirred at room temperature for 3 h and 50° C. for 3 h. The mixture was diluted with EtOAc, washed with 1N HCl, Sat. NaHCO3, brine, dried and concentrated to give ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylate (810 mg).

Aufarbeitung

  1. washwashed with 1N HCl, Sat. NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f5f0e7ef35740929a7bdd0dedca2103
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853230B2

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