4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 68583496, Verbindung

HRID 1989017

Reaktionsgleichung

Reaktionsgleichung von HRID 1989017
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].[CH2:15]([O:17][C:18]([C:20]1[C:21](Cl)=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:15]([O:17][C:18]([C:20]1[C:21]([N:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16]

Komponenten

5

Edukt 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 243063Ethyl 3-(cyclohexylamino)propanoate

Produkt 1

HCID 68583496HCID 68583496, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Cyclohexylamino-propionic acid ethyl ester (1.0 g, 5.0 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.17 g, 5.02 mmol) were combined in DCM (15 mL) and diisopropylethylamine (0.81 g, 6.3 mmol) was added. After 16 h, the solution was partitioned between water and DCM and the organic layer was dried (MgSO4) and concentrated. Chromatography (0-20% EtOAc/hexanes gradient) provided 1.63 g (84%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.39 (s, 1H) 5.30 (s, 1H), 4.30 (q, 2H, J=7.1 Hz), 4.14 (q, 1H, J=7.1 Hz), 3.76-3.80 (m, 2H), 2.65-2.69 (m, 2H), 2.49 (s, 3H), 1.81-1.84 (m, 2H), 1.34-1.40 (m, 7H), 1.12-1.27 (m, 7H).

Aufarbeitung

  1. customthe solution was partitioned between water and DCM
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-885d4f060d6e4008ad5740447204df58
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642270B2

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