2-Methyl-2-thiopseudourea → HCID 178418871, Verbindung

HRID 1696436

Reaktionsgleichung

Reaktionsgleichung von HRID 1696436
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:11][O:12]CC)[C:6](OCC)=O)[CH3:2].[CH3:16][S:17][C:18](=[NH:20])[NH2:19].CC[O-].[Na+]>CCO>[CH2:1]([O:3][C:4]([C:5]1[C:11]([OH:12])=[N:19][C:18]([S:17][CH3:16])=[N:20][CH:6]=1)=[O:15])[CH3:2]

Komponenten

5

Edukt 3

HCID 51422-Methyl-2-thiopseudoureaHCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxide

Produkt 1

HCID 178418871HCID 178418871, VerbindungAusbeute 158,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 2-ethoxymethylenemalonic acid diethyl ester (59.0 g, 273 mmol) in EtOH (300 mL) was added 2-methyl-isothiourea (41.5 g, 150 mmol) in an ice-H2O bath. An EtOHic solution of EtONa (2M, 300 mL) was added dropwise maintaining the reaction temperature under 5° C. The mixture was warmed to RT and stirred for 3 h. After standing overnight, the solvent was removed under reduced pressureand the residue was dissolved in H2O (800 mL) at 0° C. The solution was acidified to pH 3 with conc. HCl and the precipitate collected by filtration and air-dried to yield 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester as a white solid (50.8 g, 87.6% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.48 (s, 1H), 4.20 (q, J=9.6 Hz, 2H), 2.51 (s, 3H), 1.23 (t, J=9.6 Hz, 3H).

Aufarbeitung

  1. temperatureThe mixture was warmed to RT
  2. waitAfter standing overnight
  3. customthe solvent was removed
  4. dissolutionwas dissolved in H2O (800 mL) at 0° C
  5. filtrationthe precipitate collected by filtration
  6. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-fd915514089444d8a0eae3c0f5d8585e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163756B2

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