Hydrochloric Acid → HCID 90038088, compound

HRID 526014Notes

Reaction equation

HRID 526014 reaction equation
[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:11])[N:3]=1.Cl>C1COCC1>[NH2:7][CH2:6][C:5]1[CH:8]=[C:9]([I:10])[C:2]([NH2:1])=[N:3][C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90040196HCID 90040196, compound

Product 1

HCID 90038088HCID 90038088, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Amino-5-iodo-2-methylnicotinonitrile (3.70 g, 14.2 mmol) were initially charged in THF (45 ml), and 42.8 ml (42.8 mmol) of a 1 molar borane-THF complex solution in THF were added dropwise. The mixture was heated at reflux temperature for 3 hours and cooled, and 5 ml of a 2N HCl solution were cautiously added dropwise. The reaction mixture was heated under reflux for another hour and then allowed to cool for 15 hours while standing. The solvent was removed under reduced pressure and the residue was taken up in saturated sodium bicarbonate solution, which was subsequently extracted repeatedly with ethyl acetate. After drying over magnesium sulphate, the solvent was removed under reduced pressure, giving 2.50 g (60.0% of theory) of 5-(aminomethyl)-3-iodo-6-methylpyridine-2-amine, which was directly reacted further. HPLC-MS: log P=0.73; mass (m/z): 264.0

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. temperaturecooled
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for another hour
  6. temperatureto cool for 15 hours
  7. customThe solvent was removed under reduced pressure
  8. extractionwhich was subsequently extracted repeatedly with ethyl acetate
  9. dry with materialAfter drying over magnesium sulphate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5a86484f38cf456d86a75ca501a48a74
Source dataset
uspto-grants-2016_05
Patent number
US09345247B2

Reaction notes

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