Ammonia → 6-Chloro-2-methylsulfanylpyrimidine-4-carboxamide

HRID 68302

Reaktionsgleichung

Reaktionsgleichung von HRID 68302
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([S:12][CH3:13])[N:6]=1)=O.[NH3:14]>C(Cl)(Cl)Cl>[Cl:11][C:9]1[N:8]=[C:7]([S:12][CH3:13])[N:6]=[C:5]([C:3]([NH2:14])=[O:2])[CH:10]=1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 238726Methyl 6-chloro-2-(methylsulfanyl)pyrimidine-4-carboxylate

Produkt 1

HCID 2392766-Chloro-2-methylsulfanylpyrimidine-4-carboxamideAusbeute 103,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A 500 mL flask was charged with the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (4.37 g, 20 mmol), and chloroform (30 mL). Ammonia (57 mL, 7 M in methanol, 0.4 mol, 20 eq.) was added with stirring. HPLC analysis after 20 minutes indicated no starting methyl ester remained. The mixture was sparged with nitrogen for 30 min, then concentrated in vacuo, and dried under high vacuum to afford the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide (4.21 g, quant.) in sufficient purity for use in the next step. 1H NMR (500 MHz, CDCl3) □ 7.76 (s, 1H), 7.60 (br s, 1H), 5.97 (br s, 1H), 2.61 (s, 3H); ESI-MS m/z 204.1 (M+H)+.

Aufarbeitung

  1. customThe mixture was sparged with nitrogen for 30 min
  2. concentrationconcentrated in vacuo
  3. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fbe7dfd91d8d45e19fc12674d442f8ad
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822451B2

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