Potassium Carbonate → HCID 178433158, Verbindung

HRID 1371221

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[CH3:18][C@H:19]([NH:28][CH3:29])[C@H:20]([OH:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:29][N:28]([C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2[C:3]=1[N:11]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=2)[CH:19]([CH3:18])[CH:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:27]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a 5-mL, Wheaton vial were added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1 (e)) (100 mg, 0.41 mmol) and ephedrine hydrochloride (Aldrich Chemical Company) (410 mg, 2.1 mmol), followed by addition of a solution of potassium carbonate (0.71 g, 5.1 mmol) in water (2.5 mL). The reaction mixture was stirred at 120° C. for 20 h, allowed to cool to room temperature and extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated in vacuo to give a brown residue, which was purified by flash chromatography on silica gel with 1:1 EtOAc/hexanes as eluant to give 23 mg (15%) of the title compound as a tan solid. 1H NMR (DMSO-d6; 400 MHz): d 1.21 (d, 3, J=6.8), 2.42 (s, 3), 3.21 (s, 3), 4.91 (m, 1), 5.02 (m, 1), 5.87 (br s, 1), 6.69 (s, 1), 7.18-7.85 (m, 10), 10.73 (br s, 1). MS m/z: 373 (M+1), 371 (M−1).

Aufarbeitung

temperatureto cool to room temperature
extractionextracted with CH2Cl2
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customto give a brown residue, which
customwas purified by flash chromatography on silica gel with 1:1 EtOAc/hexanes as eluant

Quellen und Nachweise

ORD-Eintrag: ord-24279bd221624d47a4553d839a01e33d
Quelldatensatz: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06583154B1

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