Triethylamine → Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate

HRID 79140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79140
C(N(CC)CC)C.Cl[C:9]1[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1.[CH:19]1([NH:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:19]1([N:24]([C:9]2[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=2)[CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22080509Methyl 2-(cyclopentylamino)acetateHCID 594193864-Chloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Produkt 1

HCID 58299719Methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (10.9 mL, 78.2 mmol) was added to a solution of compound 224 (12.3 g, 65.2 mmol) and compound 225 (12.8 g, 81.5 mmol) in THF (200 mL). The reaction was stirred at room temperature. After 6 h, the reaction contents were poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organics were dried over MgSO4 and concentrated in vacuo. The crude material was crystallized from ethyl acetate and hexanes to afford methyl 2-(cyclopentyl(5-formyl-2-(methylthio)pyrimidin-4-yl)amino)acetate (226) (17.55 g, 87.0% yield).

Aufarbeitung

  1. customthe reaction contents
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was crystallized from ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-244b2a2c9db244e0850d2ccd5f4c33ce
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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