Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate → Methyl 4-methoxypyrimidine-5-carboxylate

HRID 2264162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264162
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=[C:5](SC)[N:4]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][N:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 2

HCID 12828997Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12828992Methyl 4-methoxypyrimidine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2.2 g of methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate, 15 g of Raney nickel (washed with methanol to remove water) and 200 mL of methanol was stirred under 1 atm hydrogen overnight. Conversion was incomplete by LCMS so the mixture was filtered and treated with 15 g of fresh Raney nickel under hydrogen overnight. After filtration and concentration under reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes) gave the product as white crystalline solid: MS (m+1)=169.1; 1H NMR (400 MHz, CDCl3) 9.0 (s, 1H), 8.82 (s, 1H), 4.1 (s, 3H), 3.9 (s, 3H).

Aufarbeitung

  1. filtrationwas filtered
  2. additiontreated with 15 g of fresh Raney nickel under hydrogen overnight
  3. filtrationAfter filtration and concentration
  4. customunder reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7f4a2c62b43e43edba2533c7006ab1ca
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855201B2

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