4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 849409, Verbindung
Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH2:15][C:16]1[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:15][C:16]2[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (4.6 g, 19.6 mmol) in ethanol (90 mL) is added 5-amino-1,3-dimethylpyrazole (4.4 g, 39.2 mmol). The mixture is heated for 22 hours at 80° C. The reaction is cooled to room temp and concentrated in vacuo. The solid which remains is dissolved in CHCl3 and washed with aqueous saturated NaHCO3 solution. The organic phase is dried (MgSO4), filtered and concentrated in vacuo and the resulting residue is purified over silica (50% EtOAc//hexanes, followed by 100% EtOAc) to afford 4.8 g of the desired product: 1H NMR (300 MHz, CDCl3) δ10.29 (s, NH), 8.82 (s, 1H), 6.30 (s, 1H), 4.43 (q, J=7.2 Hz, 2H), 3.77 (s, 3H), 2.53 (s, 3H), 2.30 (s, 3H), 1.45 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 308.0 (100, M++H).
Aufarbeitung
- temperatureThe reaction is cooled to room temp
- concentrationconcentrated in vacuo
- dissolutionThe solid which remains is dissolved in CHCl3
- washwashed with aqueous saturated NaHCO3 solution
- dry with materialThe organic phase is dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customthe resulting residue is purified over silica (50% EtOAc//hexanes, followed by 100% EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-448fe476ba9c4e8db6c2440cfb53c2bf
- Quelldatensatz
- uspto-grants-2008_01
- Patentnummer
- US07319102B1
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