5-Aminopyridine-2-carbonitrile → HCID 55295868, compound

HRID 1040435Notes

Reaction equation

HRID 1040435 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][CH2:11][Mg+].[Br-]>C1COCC1.O.Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[NH2:9][C:8]1([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 2

HCID 38713955-Aminopyridine-2-carbonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 55295868HCID 55295868, compoundYield 831.6%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-cyanopyridine (1.0 g, 8.06 mmol) in dry THF (50 mL) was added titanium(IV) isopropoxide (5.2 mL, 17.7 mmol). EtMgBr (3.0M in Et2O, 10.7 mL, 32.2 mmol) was then added dropwise. The reaction mixture was stirred for 23 h, then diluted with water (100 mL) and 1N HCl (5 mL), and stirred for 5 min. The mixture was filtered and the filtrate was concentrated in vacuo to afford 6-(1-amino-cyclopropyl)-pyridin-3-ylamine as brown oil (10 g) which was used without further purification.

Workup

  1. stirringstirred for 5 min
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7605db2382da4a2c9f735f798b9e6b71
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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