Potassium Carbonate → 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine

HRID 1609852

Reaktionsgleichung

[Cl:1][C:2]1[C:3]([CH2:10]Cl)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH2:10][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[N:18]=[CH:19][CH:20]=[CH:21][N:22]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

A mixture of 3-chloro-2-chloromethyl-5-methoxy pyrazine (141 mg, 0.73 mmol), 2-(1H-imidazol-2-yl)-pyrimidine (105 mg, 0.72 mmol) and K2CO3 (307 mg, 2.22 mmol) in DMF (10 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (5 mL) and extracted with DCM (3×15 mL). The combined organic layers are dried and solvent removed. PTLC separation (silica gel; 10% MeOH in DCM) gives 120 mg of 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine as an oil. 1H NMR (CDCl3) 8.98 (d, 2H), 7.98 (s, 1H), 7.27 (s, 1H), 7.14–7.18 (m, 2H), 6.05 (s, 2H), 3.97 (s, 3H). H. 2-[1-(3,5-Dimethoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine (Compound 9)

Aufarbeitung

temperatureOn cooling
customthe reaction is quenched with saturated NH4Cl (5 mL)
extractionextracted with DCM (3×15 mL)
customThe combined organic layers are dried
customsolvent removed
customPTLC separation (silica gel; 10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag: ord-26e53d8579d04b74809dc7cba56e8b1b
Quelldatensatz: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06982268B2

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