N,N-Dimethylaniline → (S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

HRID 1534404

Reaktionsgleichung

Reaktionsgleichung von HRID 1534404
Cl[C:2]1(Cl)[C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=2)[NH:3]1.C[C@@H](CC)CBr.C(OCC)(=O)CC(OCC)=O.C[O-].[Na+].Cl.C(OC1C=CC(C(N)=N)=CC=1)CCCCCC.OC1C(C[C@@H](C)CC)=C(O)N=C(C2C=CC(OCCCCCCC)=CC=2)N=1.CN(C)C1C=CC=CC=1.[H][H]>[Pd].C(N(CC)CC)C.CO>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[N:3]=[CH:2][C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

12

Edukt 8

HCID 949N,N-DimethylanilineHCID 7761Diethyl MalonateHCID 54641671-Bromo-2-methylbutane, (+)-HCID 10942334Sodium MethoxideHCID 12238503p-Heptyloxybenzamidine hydrochlorideHCID 178418361HCID 178418361, VerbindungHCID 178444044(S)-4,4-dichloro-2-(p-heptyloxy-phenyl)-5-(2-methylbutyl)-pyrimidineHCID 178444047HCID 178444047, Verbindung

Produkt 1

HCID 53993226(S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 40 g of (S)-4,4-dichloro-2-(p-heptyloxy-phenyl)-5-(2-methylbutyl)-pyrimidine [obtainable by reacting (S)-2-methylbutyl bromide with diethyl malonate in the presence of sodium methanolate, followed by condensation of the resultant diethyl (S)-2-methylbutyl malonate with p-heptyloxybenzamidine hydrochloride, and reacting the resultant (S)-4,6-dihydroxy-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine with phosphoroxy trichloride and dimethylaniline], 400 ml of methanol, 40 ml of triethylamine and 20 g of Pd-C (5%) is hydrogenated at room temperature under normal pressure until the theoretical amount of hydrogen has been taken up. After filtering off the catalyst and distilling off the solvent, the residue is recrystallized from ethanol. (S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine is obtained.

Aufarbeitung

  1. filtrationAfter filtering off the catalyst
  2. distillationdistilling off the solvent
  3. customthe residue is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2a73b81a81b34ad481b09ae855becb02
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089168

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