Water → HCID 58710598, compound

HRID 646753Notes

Reaction equation

HRID 646753 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]O)[CH:13]=2)[N:6]=1)=[O:4].C1(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.O>C1COCC1>[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:34]=[N+:35]=[N-:36])[CH:13]=2)[N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 10355149HCID 10355149, compound

Product 1

HCID 58710598HCID 58710598, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-6-(3-hydroxymethyl-phenyl)-pyrazine-2-carboxylic acid methylamide (1.00 g, 3.87 mmol) was dissolved in THF (20 mL) followed by the addition of diphenylphosphoryl azide (0.63 mL, 5.42 mmol) and DBU (0.43 mL, 5.42 mmol). 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 filteration, concentration and purified by column chromatography (50% Ethylacetae/bexanes) to give 3-amino-6-(3-azidomethyl-phenyl)-pyrazine-2-carboxylic acid methylamide, 728 mg (66.4% yield): MS (EI) for C13H13N7O0: 284.12 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialthen dried over anhydrous sodium sulfate and filteration, concentration
  3. custompurified by column chromatography (50% Ethylacetae/bexanes)

Sources & evidence

ORD record
ord-5b96adb87059481f8956b8908eb5911e
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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