Diethyl 2-(p-tolyl)malonate → 5-(4-Methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidine

HRID 1082313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1082313
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]([O:16]CC)=O)[C:9]([O:11]CC)=O)=[CH:4][CH:3]=1.Cl.[C:20]([NH2:25])(=[NH:24])[CH2:21][CH2:22][CH3:23].C[O-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([OH:11])=[N:24][C:20]([CH2:21][CH2:22][CH3:23])=[N:25][C:14]=2[OH:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 570878Diethyl 2-(p-tolyl)malonateHCID 10942334Sodium MethoxideHCID 12828983Butanimidamide hydrochloride

Produkt 1

HCID 1784184665-(4-Methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidineAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of diethyl (4-methylphenyl)malonate (9.45 g) and butyramidine hydrochloride (5.00 g) in methanol (25 ml) is added 28% sodium methoxide (19.67 g) under ice-cooling, and the mixture is stirred at room temperature overnight. After the reaction is complete, the reaction solution is concentrated to the half volume thereof, and the resultant is diluted with water. The mixture is acidified with 10% hydrochloric acid, and the precipitated crystals are collected by filtration, washed, and dried to give 5-(4-methylphenyl)-4,6-dihydroxy-2-n-propylpyrimidine (5.17 g) as crystalline powder.

Aufarbeitung

  1. temperaturecooling
  2. concentrationthe reaction solution is concentrated to the half volume
  3. additionthe resultant is diluted with water
  4. filtrationthe precipitated crystals are collected by filtration
  5. washwashed
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c5afd419830c46a6a30bf470ed776439
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589478

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