Potassium Carbonate → HCID 22248994, compound

HRID 2170195Notes

Reaction equation

HRID 2170195 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:8][C:4]1[N:3]=[C:2]([NH:16][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 785042,6-Dichloropyrazine

Product 1

HCID 22248994HCID 22248994, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloropyrazine (4.00 g, 26.8 mmol) and 4-methoxybenzylamine (7.02 mL, 53.7 mmol) in DMF (30 mL) was added K2CO3 (7.42 g, 53.7 mmol) at RT and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with cold water (100 mL) and extracted into ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give a residue that was purified by CombiFlash (REDISEP®, silica gel, 24 g, 25% EtOAc/petroleum ether) to give 6-chloro-N-(4-methoxybenzyl)pyrazin-2-amine (5.00 g, 74.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.31 (s, 3H), 4.37 (d, J=6.0 Hz, 2H), 6.87-6.93 (m, 2H), 7.24-7.31 (m, 2H), 7.70 (s, 1H), 7.90 (s, 1H), 7.95 (t, J=5.5 Hz, 1H).

Workup

  1. extractionextracted into ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give a residue that
  6. customwas purified by CombiFlash (REDISEP®, silica gel, 24 g, 25% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-eba139ec379e448eb6da89c605f16a10
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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