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

HRID 1762920

Reaktionsgleichung

Reaktionsgleichung von HRID 1762920
Cl[C:2]1[C:7]([CH2:8][C@@H:9]([CH3:12])[CH2:10][CH3:11])=[C:6](Cl)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=2)[N: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>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([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:15][CH:16]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

12

Edukt 8

HCID 949N,N-DimethylanilineHCID 7761Diethyl MalonateHCID 54641671-Bromo-2-methylbutane, (+)-HCID 10942334Sodium MethoxideHCID 12238503p-Heptyloxybenzamidine hydrochlorideHCID 86743091(S)-4,6-dichloro-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidineHCID 178418361HCID 178418361, VerbindungHCID 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)-4,6-dichloro-2-(p-heptyloxyphenyl)-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-767731b3f31644a4a2cb234f2c8e26af
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04834904

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