Sodium Hydroxide → 6-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid

HRID 68293

Reaktionsgleichung

Reaktionsgleichung von HRID 68293
O=[C:2]([CH2:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[C:3]([OH:5])=[O:4].S(O)(O)(=O)=O.[CH3:22][S:23][C:24](=[NH:26])[NH2:25].[O-]CC.[Na+].[OH-].[Na+]>C(O)C>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[N:26]=[C:24]([S:23][CH3:22])[N:25]=[C:2]([C:3]([OH:5])=[O:4])[CH:6]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfateHCID 5106694-(2-Methoxyphenyl)-2,4-dioxobutanoic acidHCID 2723922Sodium ethoxide

Produkt 1

HCID 393752796-(2-Methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2,4-dioxo-4-(2-methoxyphenyl)butyric acid (15.6 g, 70 mmol), 2-methyl-isothiourea sulfate (10.4 g, 73.5 mmol) and sodium ethoxide (26 mL, 21% by wt. in ethanol, 70 mmol) in ethanol (200 mL) was heated to reflux overnight. The resulting solution was reduced to approximately 50 mL using a rotary evaporator, water (200 mL) was added to give a suspension, which was adjusted to pH >9 with 10% NaOH. The mixture was extracted with diethyl ether (100 mL). The aqueous layer was taken to pH=3 with conc. HCI solution to give a suspension, which was heated to 90° C. for 10 minutes. Upon cooling in an ice bath for 1 h, a precipitate formed, which was filtered, washed with water (20 mL), and dried overnight under vacuum to give 6-(2-methoxyphenyl)-2-(methylthio)pyrimidine-4-carboxylic acid. 1H NMR (300 MHz, CDCl3) δ 8.45 (s, 1H), 8.10 (dd, J=7.5, 1.8 Hz, 1H), 7.48 (m, 1H), 7.09 (t, J=6.9 Hz, 1H), 7.02 (d, J=8.7 Hz, 1H), 3.94 (s, 3H), 2.67 (s, 3H). HPLC ret. time 2.02 min, 10-100% CH3CN, 5 min gradient; ESI-MS m/z 277.1 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customa rotary evaporator, water (200 mL)
  4. additionwas added
  5. customto give a suspension, which
  6. extractionThe mixture was extracted with diethyl ether (100 mL)
  7. customto give a suspension, which
  8. temperatureUpon cooling in an ice bath for 1 h
  9. customa precipitate formed
  10. filtrationwhich was filtered
  11. washwashed with water (20 mL)
  12. customdried overnight under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e98127463b7d48738a90402cb5dfb724
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822451B2

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