Water → HCID 86046572, compound

HRID 2217214Notes

Reaction equation

HRID 2217214 reaction equation
[NH2:1][C:2]1[C:3]([C:17]#[N:18])=[N:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[CH:6][N+:7]=1[O-].P(Cl)(Cl)([Cl:21])=O.O>COCCOC>[NH2:1][C:2]1[C:3]([C:17]#[N:18])=[N:4][C:5]([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[C:6]([Cl:21])[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178488799HCID 178488799, compound

Product 1

HCID 86046572HCID 86046572, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Amino-6-(6-methoxy-3-pyridyl)-2-pyrazinecarbonitrile 4-oxide (6.65 g) was dissolved in DME (133 ml). To the solution was added phosphorus oxychloride (12.6 g) at 25° C. The mixture was stirred at ambient temperature for 2 hours. To the mixture was added water (520 ml). The solution was stirred at 20-25° C. for 15 hours. The precipitated crystals were collected by filtration and dried in vacuo, to give 3-amino-5-chloro-6-(6-methoxy-3-pyridyl)-2-pyrazinecarbonitrile as powder (4.6 g). The filtrate was extracted with EtOAc. The organic solution was washed with brine, dried over MgSO4. Evaporation of solvent in vacuo gave oily residue. The residue was purified by chromatography on silica gel (EtOAc:n-Hexane=1:1, v/v) to give 3-amino-5-chloro-6-(6-methoxy-3-pyridyl)-2-pyrazinecarbonitrile as powder (1.0 g).

Workup

  1. stirringThe solution was stirred at 20-25° C. for 15 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-58d3dd8329b347cdaa3da2d0f6e7cd3b
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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