Hydrochloric Acid → Methyl (4,6-dimethoxypyrimidin-2-yl)carbamate

HRID 364843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 364843
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl.[Cl-].[Na+]>O1CCCC1>[CH3:14][O:15][C:16](=[O:17])[NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1189462-Amino-4,6-dimethoxypyrimidine

Produkt 1

HCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-Amino-4,6-dimethoxypyrimidine (56 g) was added portionwise to 50% sodium hydride (42.8 g) in 1000 ml of dry tetrahydrofuran. After stirring for 0.5 hour, dimethylcarbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for about 16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly as external cooling was used to maintain a pot temperature of about 25° C. Saturated aqueous sodium chloride (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over sodium sulfate. Filtering and evaporating the solvents afforded the crude material which was recrystallized from hexane to yield 54 g of the title compound, m.p. 81°-83° C. The IR spectrum showed characteristic absorption bands at 3400 and 1760 cm-1.

Aufarbeitung

  1. temperaturewith cooling
  2. stirringThe mixture was stirred under nitrogen for about 16 hours at ambient temperature
  3. temperatureas external cooling
  4. customThe solvents were decanted from the precipitated solids
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltering
  7. customevaporating the solvents
  8. customafforded the crude material which
  9. customwas recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-4ecbfa32b96b49de9eba3c73f4efbbd0
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04606755

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