Triphenylphosphine → HCID 58710591, compound

HRID 646754Notes

Reaction equation

HRID 646754 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]=[N+]=[N-])[CH:13]=2)[N:6]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[CH3:1][NH:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=2)[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 58710598HCID 58710598, compound

Product 1

HCID 58710591HCID 58710591, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-6-(3-azidomethyl-phenyl)-pyrazine-2-carboxylic acid methylamide was dissolved in the mixture of THF (15 mL) and H2O (1.5 mL) followed by the addition of triphenylphosphine (1.07 g, 4.03 mmol) and it was stirred at room temperature overnight. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate (2×50 mL) then dried over anhydrous sodium sulfate and filtered, concentrated and purified by column chromatography (50% Ethylacetae/hexanes) to give 3-amino-6-(3-aminomethyl-phenyl)-pyrazine-2-carboxylic acid methylamide, 564 mg (85.0% yield): MS (EI) for C13H15N5O: 258.13 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialthen dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (50% Ethylacetae/hexanes)

Sources & evidence

ORD record
ord-c2874d060fab421d8026038983ec3eb3
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…