Hydrochloric Acid → HCID 18677512, compound

HRID 1634210Notes

Reaction equation

HRID 1634210 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[N:10]=1)[C:5]([NH2:7])=O.CSC.Cl.[OH-].[Na+]>C1COCC1>[NH2:7][CH2:5][C:4]1[CH:8]=[C:9]([NH2:11])[N:10]=[C:2]([NH2:1])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 18677496HCID 18677496, compound

Product 1

HCID 18677512HCID 18677512, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing suspension of 0.5 g (3.29 mmol) 2,6-diamino-isonicotinamide in 3 ml THF was added dropwise 0.455 ml (4.8 mmol) boran-dimethylsulfide-complex and the mixture was refluxed for 4 d. After cooling to room temperature 0.548 ml 6N HCl was added and the mixture was neutralized with 2N NaOH. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica eluting with DCM:MeOH:NH3aq. 100:100:1 to yield 166 mg (36%) of the title compound as yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 4 d
  2. additionwas added
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-8154d2e2331c4712bd449e0fca922481
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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