3-Anilinopropionitrile → 4-[(2-Cyano-ethyl)-phenyl-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

HRID 1989013

Reaktionsgleichung

Reaktionsgleichung von HRID 1989013
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[C:15]1([NH:21][CH2:22][CH2:23][C:24]#[N:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:11]([O:10][C:8]([C:7]1[C:2]([N:21]([CH2:22][CH2:23][C:24]#[N:25])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:3][C:4]([S:13][CH3:14])=[N:5][CH:6]=1)=[O:9])[CH3:12]

Komponenten

3

Edukt 2

HCID 141003-AnilinopropionitrileHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Produkt 1

HCID 686776284-[(2-Cyano-ethyl)-phenyl-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

Versuchsvorschrift

The title compound was prepared from ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (3.7 g, 15.8 mmol) and 3-phenylamino-propionitrile (2.3 g, 15.8 mmol) according to the procedure outlined in Example 1 (B). The product was purified chromatographically (silica, EtOAc/hexanes 1:20-1:2, v/v). A white solid was obtained (3.5 g, 65%). 1H NMR (300 MHz, CDCl3) δ (ppm): 8.32 (s, 1H), 7.34(m, 2H), 7.20 (m, 1H), 7.13 (m, 2H), 4.32 (t, J=7.1 Hz, 2H), 3.56 (q, J=7.1 Hz, 2H), 2.75 (t, J=7.1 Hz, 2H), 2.55 (s, 3H), 1.00 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. customThe product was purified chromatographically (silica, EtOAc/hexanes 1:20-1:2
  2. customA white solid was obtained (3.5 g, 65%)

Quellen und Nachweise

ORD-Eintrag
ord-d0839dcb1b0a4729b5e41dfaa95312fe
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642270B2

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