Reaktion #10336

Reaktionsgleichung

dimethyl-(o-methoxyphenoxy)malonate

Sodium methylate

acetamidine hydrochloride

→

5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine

Ausbeute 69.3%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   FiltrationThe solid was filtered off
3. 3
   Waschenwashed with another portion of diethyl ether (100 ml)
4. 4
   workup.DISSOLUTIONdissolved in water (50 ml)
5. 5
   workup.ADDITIONby adding glacial acetic acid (25 ml)
6. 6
   SonstigeThe white precipitate that formed
7. 7
   Filtrationwas filtered off
8. 8
   Waschenwashed with water
9. 9
   Sonstigedried

Vorschrift

A solution of dimethyl-(o-methoxyphenoxy)malonate (10 g) in dry methanol (80 ml) was cooled to 0° C. Sodium methylate (6.71 g) was added portionwise. To the suspension was added of acetamidine hydrochloride (2.84 g) and the mixture was stirred overnight at r.t. The solvent was removed under reduced pressure and the residue was suspended in diethyl ether (100 ml). The solid was filtered off, washed with another portion of diethyl ether (100 ml) and dissolved in water (50 ml). The pH was adjusted to 4 by adding glacial acetic acid (25 ml). The white precipitate that formed was filtered off, washed with water and dried to yield 5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine (5.17 g) (or a tautomer) as a white powder.

Quelle