Potassium Carbonate → HCID 10425067, compound

HRID 1609846Notes

Reaction equation

HRID 1609846 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.[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18]1[S:19][CH:20]=[CH:21][N:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:10][O:9][C:8]1[C:3]([CH2:2][N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[N:4][CH:5]=[C:6]([O:11][CH3:12])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22260391HCID 22260391, compoundHCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazole

Product 1

HCID 10425067HCID 10425067, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2-chloromethyl-3,5-dimethoxy-pyrazine (140 mg, 0.74 mmol), 2-(1H-imidazol-2-yl)-thiazole (106 mg, 0.70 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 (silica gel) separation (10% MeOH in DCM) gives 170 mg of 3,5-dimethoxy-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-pyrazine as an oil. 1H NMR (CDCl3) 7.80 (d, 1H), 7.68 (s, 1H), 7.32 (d, 1H), 7.09 (s, 1H), 6.98 (s, 1H), 5.97 (s, 2H), 3.92 (s, 3H) 3.87 (s, 3H). E. 3-Chloro-2-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-methoxy-pyrazine (Compound 6) 1. Preparation of 3-Chloro-5-methoxy-pyrazine-2-carbaldehyde

Workup

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

Sources & evidence

ORD record
ord-7e4e8a52306045a1bb986772891e10a3
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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