Acetonitrile → HCID 178499065, Verbindung

HRID 1172053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172053
[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9](N)[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20][CH3:21])[C:14]=2[F:22])[N:6]=1)=[O:4].C(#N)C.N([O-])=[O:27].[Na+]>OS(O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:11])=[C:9]([OH:27])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([O:20][CH3:21])[C:14]=2[F:22])[N:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 166568016-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl esterHCID 23668193Sodium Nitrite

Produkt 1

HCID 178499065HCID 178499065, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl ester (320 mg, 0.92 mmol, see U.S. Pat. No. 7,300,907 B2 for preparation) was dissolved in 10 mL 1M H2SO4 plus 4 mL acetonitrile, warmed to 75° C. and treated in portions with sodium nitrite (690 mg, 10 mmol) over 30 minutes. After stirring for 10 minutes more the mixture was cooled and the solid product was collected by filtration, washed well with water, and dried under vacuum at 80° C. to give 170 mg (53% yield) of 6-hydroxy-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-chloropyrimidine-4-carboxylic acid methyl ester MP 215-217° C.; MS m/z 346; 1H NMR (DMSO-d6): δ 7.47 (m, 2H), 3.94 (s, 3H), 3.91 (s, 3H), 3.34 (br s, 1H).

Aufarbeitung

  1. temperaturewas cooled
  2. filtrationthe solid product was collected by filtration
  3. washwashed well with water
  4. customdried under vacuum at 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-f2439570edf84fc7bd881d6b788bb82c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833940B2

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