Ethyl Acetate → HCID 70285636, compound

HRID 235072Notes

Reaction equation

HRID 235072 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[N:6][CH:5]=[CH:4][N:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH2:11][OH:12].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:10]([C:11]1[O:12][C:2]2[N:3]=[CH:4][CH2:5][NH:6][C:7]=2[C:8]=1[NH2:9])([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66774Methyl GlycolateHCID 2924653-Chloropyrazine-2-carbonitrile

Product 1

HCID 70285636HCID 70285636, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3-cyanopyrazine (0.751 g, 5.38 mmol) was treated with methyl glycolate (0.533 g, 5.92 mmol) and potassium carbonate (1.12 g, 8.07 mmol) in 20 ml DMF as described in Example 85A. Column chromatograhpy on silica gel eluting with 1:1 hexanes:ethyl acetate gave the title compound (0.33 g, 32%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ4.02 (s, 3H), 5.29 (br s, 2H), 8.47 (d, 1H), 8.56 (d, 1H). MS (DCI/NH3) m/e 194 (M+H)+, 211 (M+NH4)+.

Sources & evidence

ORD record
ord-cf3ab0836f864e4caf4a3a9d8d97182d
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

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