Triethylamine → Ethyl 2-(4-butoxyphenyl)pyrimidine-5-carboxylate

HRID 1195614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195614
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[H][H].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 2

HCID 8471TriethylamineHCID 3614036HCID 3614036, Verbindung

Produkt 1

HCID 13907408Ethyl 2-(4-butoxyphenyl)pyrimidine-5-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 178418361HCID 178418361, VerbindungLösungsmittel

Versuchsvorschrift

This compound (V) (3.3 g, 10 mmols) was dissolved in ethyl acetate (30 ml), followed by agitating the solution together with Pd/C (5%) (0.6 g) and triethylamine (1.0 g) in hydrogen atmosphere at room temperature for 3 hours, filtering off Pd/C, adding toluene (100 ml), washing the resulting fluid with 2N-hydrochloric acid (50 ml), washing it with water till the washing water became pH 7, drying the toluene phase over anhydrous magnesium sulfate, filtering off magnesium sulfate, concentrating under reduced pressure to obtain white crystals and recrystallizing the crystals from methanol to obtain ethyl-2-(4-butyloxyphenyl)-5-pyrimidinecarboxylate (VI) (2.4 g) (yield: 80%) having a melting point 99.1° C.

Aufarbeitung

  1. filtrationfiltering off Pd/C
  2. additionadding toluene (100 ml)
  3. washwashing the resulting fluid with 2N-hydrochloric acid (50 ml)
  4. washwashing it with water till the washing water
  5. dry with materialdrying the toluene phase over anhydrous magnesium sulfate
  6. filtrationfiltering off magnesium sulfate
  7. concentrationconcentrating under reduced pressure
  8. customto obtain white crystals
  9. customrecrystallizing the crystals from methanol

Quellen und Nachweise

ORD-Eintrag
ord-df3701453e05455f9bfd5954154153f1
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112523

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