Aniline → 4-Chloro-2-methylsulfanyl-6-phenylamino-pyrimidine-5-carbonitrile

HRID 644778

Reaktionsgleichung

Reaktionsgleichung von HRID 644778
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO.CCOCC>[Cl:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Komponenten

5

Edukt 2

HCID 6115AnilineHCID 42016204,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Produkt 1

HCID 35765124-Chloro-2-methylsulfanyl-6-phenylamino-pyrimidine-5-carbonitrileAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile [Santilli, et al., J. Heterocycl. Chem. 1971, 8, 445-453] (0.222 grams (hereinafter “g”), 1.0 millimoles (hereinafter “mmol”)) in EtOH (2 milliliters (hereinafter “mL”)) and Et2O (1 mL) was treated with aniline (184 microliter (hereinafter “uL”), 2.0 mmol) in EtOH (1 mL). A clear solution formed initially but rapidly formed a heavy precipitate. The mixture was stirred 30 minutes (hereinafter “min”) and was filtered, and the solid was washed with 1:1 Et2O, EtOH and then Et2O, dried to afford 162 miligrams (hereinafter “mg”) (59%) of the title compound as a white solid. LC MS m/e=277 (MH+), Rt=2.32 min.

Aufarbeitung

  1. customA clear solution formed initially
  2. customrapidly formed a heavy precipitate
  3. filtrationwas filtered
  4. washthe solid was washed with 1:1 Et2O, EtOH
  5. dry with materialEt2O, dried

Quellen und Nachweise

ORD-Eintrag
ord-121a4b7cb55f4b64847d6c82d48e1707
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700768B2

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