Hydrochloric Acid → HCID 68583787, Verbindung

HRID 12349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12349
[Na].C(O[C:5]([C:7]1[C:8]([N:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1)=[O:6])C.CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:21]([O:20][C:18]([CH:17]1[CH2:16][N:15]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:8]2[N:9]=[C:10]([S:13][CH3:14])[N:11]=[CH:12][C:7]=2[C:5]1=[O:6])=[O:19])[CH3:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 23676156Sodium t-butoxideHCID 685834964-[Cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Produkt 1

HCID 68583787HCID 68583787, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium (25 wt % dispersion in paraffin wax, 0.10 g, 3.8 mmol) was added to t-butanol (1.8 mL) at rt. After 10 minutes, a solution of 4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 2.5 mmol) in 10 mL of toluene was added to the sodium t-butoxide solution and the resulting mixture was heated at 90° C. for 30 minutes. The reaction mixture was then cooled and the solution was adjusted to pH 7 using a 1N HCl solution. The solution was then extracted with EtOAc (2×20 mL) and the organic layer was dried (MgSO4) and concentrated to provide 0.55 g (42%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. extractionThe solution was then extracted with EtOAc (2×20 mL)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41677c4f3045402cbb69067e5b147a3b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728003B2

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