Acetic Acid → HCID 90409506, compound

HRID 2177632Notes

Reaction equation

HRID 2177632 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:9][C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH:3]=1.C(O)(=O)C.[N:20](OC(C)(C)C)=O>C1COCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[N:20][N:9]([C:10]3[CH:15]=[N:14][CH:13]=[CH:12][N:11]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 90409379HCID 90409379, compound

Product 1

HCID 90409506HCID 90409506, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methyl-N4-(pyrazin-2-yl)pyridine-3,4-diamine (520 mg, 2.58 mmol) in THF (30 mL) was added acetic acid (0.44 mL, 7.75 mmol) and tert-butyl nitrite (0.51 mL, 3.88 mmol). The reaction was heated to reflux. After 30 min the reaction was cooled and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (0-7% [2M NH3 in MeOH]CH2Cl2) to give the desired product (127 mg, 25%). MS (ESI) mass calcd. C11H9N5, 212.08. m/z found, 213.1 [M+H]+.

Workup

  1. temperatureThe reaction was heated to reflux
  2. temperatureAfter 30 min the reaction was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on silica gel (0-7% [2M NH3 in MeOH]CH2Cl2)

Sources & evidence

ORD record
ord-69f7cc6c94ed4c1cba58a5a05ac46978
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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