1,2-Dimethoxyethane → HCID 86757823, compound

HRID 275765Notes

Reaction equation

HRID 275765 reaction equation
[CH3:1][N:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]1=[O:21].COCCOC.[Li+].[N:29]1[CH:34]=[CH:33][C:32](B([O-])[O-])=[CH:31][CH:30]=1.[Li+].C(=O)([O-])[O-].[Na+].[Na+]>O>[ClH:8].[CH3:1][N:2]1[C:7]([C:32]2[CH:33]=[CH:34][N:29]=[CH:30][CH:31]=2)=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]1=[O:21]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 18315859HCID 18315859, compoundHCID 70162249HCID 70162249, compound

Product 1

HCID 86757823HCID 86757823, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-methyl-3,5-diphenyl-6-chloro-1H-pyrazin-2-one (0.5 g) in 3:1 ethylene glycol dimethylether : water (30 cm3), under nitrogen, was added sequentially 4-pyridyl boronic acid lithium salt (0.42 g), sodium carbonate (0.72 g) and tetrakis-triphenylphosphine palladium (0.07 g). The reaction was heated at reflux, under nitrogen, overnight. The solvents were evaporated and the residue partitioned between water and 5% methanol/dichloromethane. The organic phase was separated, dried over magnesium sulphate and evaporated in vacuo. The residue was subjected to silica gel chromatography using 2% methanol/dichloromethane as eluant. The product was treated with hydrogen chloride in methanol and recrystallised from ethyl acetate/diethyl ether to afford 1-methyl-3,5-diphenyl-6-(4-pyridyl)-1H-pyrazin-2-one hydrochloride(0.2 g ; 32%) as yellow crystals. Found C, 70.50; H, 4.90; N, 11.20% C22H17N3O.HCl requires C, 70.30; H, 4.83; N, 11.18%.m/e (ES+) 340 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux, under nitrogen, overnight
  3. customThe solvents were evaporated
  4. customthe residue partitioned between water and 5% methanol/dichloromethane
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in vacuo
  8. additionThe product was treated with hydrogen chloride in methanol
  9. customrecrystallised from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-6799fe17465f415da90e813df5e786d8
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Reaction notes

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