Potassium Carbonate → 2-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-3,5-dimethoxy-pyrazine

HRID 1609845Notes

Reaction equation

Cl[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[N:7][C:6]([O:11][CH3:12])=[CH:5][N:4]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:13][C:14]1[N:15]=[C:16]([C:20]2[N:24]([CH2:2][C:3]3[C:8]([O:9][CH3:10])=[N:7][C:6]([O:11][CH3:12])=[CH:5][N:4]=3)[CH:23]=[CH:22][N:21]=2)[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 2-chloromethyl-3,5-dimethoxy-pyrazine (115 mg, 0.61 mmol), 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (98 mg, 0.60 mmol) and K2CO3 (250 mg, 1.81 mmol) in DMF (7 mL) is stirred at 45° C. for 16 hours. On cooling, the reaction is quenched with saturated NH4Cl (3 mL) and extracted with DCM (3×15 mL). The combined organic layers are dried and solvent removed. PTLC (silica gel) separation (10% MeOH in DCM) gives 123 mg of 2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-3,5-dimethoxy-pyrazine as an oil. LRMS calcd 315.30, found 316.20 (MH+). D. 3,5-Dimethoxy-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazinel (Compound 5)

Workup

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

Sources & evidence

ORD record: ord-7b53c740dee24e158d2d6935faf4945a
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982268B2

Reaction notes

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