2-Methyl-2-thiopseudourea sulfate → Methyl 4-tert-butyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 38760

Reaktionsgleichung

Reaktionsgleichung von HRID 38760
[CH3:1][C:2]([CH3:11])([CH3:10])[C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:12]OC(OC)N(C)C.S(O)(O)(=O)=O.[CH3:25][S:26][C:27](=[NH:29])[NH2:28].C([O-])(=O)C.[Na+]>O.CN(C)C=O>[C:2]([C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:12][N:28]=[C:27]([S:26][CH3:25])[N:29]=1)([CH3:11])([CH3:10])[CH3:1]

Komponenten

7

Edukt 4

HCID 752702-Methyl-2-thiopseudourea sulfateHCID 78373Dimethylformamide dimethyl acetalHCID 99597Methyl pivaloylacetateHCID 517045Sodium Acetate

Produkt 1

HCID 58168926Methyl 4-tert-butyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of methyl 4,4-dimethyl-3-oxopentanoate (10 g) and N,N-dimethyl formamide dimethyl acetal (9.5 mL) was stirred at 75° C. for 2 hours. To the reaction mixture were added N,N-dimethyl formamide (100 mL), S-methylisothiourea sulfate (2:1) (9.7 g), and sodium acetate (11.4 g), followed by stirring at 90° C. for 15 hours. The reaction mixture was cooled to room temperature, and water was added thereto. The aqueous layer was extracted with ethyl acetate and the organic layer was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain methyl 4-tert-butyl-2-(methylsulfanyl)pyrimidine-5-carboxylate (8.4 g) as a colorless oily substance.

Aufarbeitung

  1. stirringby stirring at 90° C. for 15 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cf7b38d4db5847fe91ef4f679d98c286
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524727B2

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