2,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile → 2,4,7-triamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile

HRID 1072257Notes

Reaction equation

HRID 1072257 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:19])[C:3]=1[C:20]#[N:21])=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3>CN(C=O)C.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([CH2:15][C:5]2=[C:4]([NH2:19])[C:3]=1[C:20]#[N:21])=[CH:13][C:12]([NH2:16])=[CH:11][CH:10]=3

Participants

4

Reactant 1

HCID 100852162,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 100836002,4,7-triamino-5H-chromeno[2,3-b]pyridine-3-carbonitrileYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-diamino-7-nitro-5H-chromeno[2,3-b]pyridine-3-carbonitrile, produced as described above, (0.55 mmol, 155 mg) and Pd/C (35 mg, 10% on activated carbon) in DMF (15 mL) was stirred under an atmosphere of hydrogen (balloon) for 3.5 hours. The catalyst was removed by filtration using a plug of celite. The filtrated was concentrated in vacuo and the residue was triturated with methanol to give 2,4,7-triamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile as a grey solid (109 mg, 79% yield). 1H NMR (300 MHz, DMSO-d6): δ 6.72 (d, J=8.0 Hz, 1H), 6.39-6.5(m, 4H), 6.25 (s, 2H), 3.52 (s, 2H); m/z 254 (M+H).

Workup

  1. customproduced
  2. customThe catalyst was removed by filtration
  3. concentrationThe filtrated was concentrated in vacuo
  4. customthe residue was triturated with methanol

Sources & evidence

ORD record
ord-0d1ff64e64ee4cf8b5d0c542d121cff5
Source dataset
uspto-grants-2005_06
Patent number
US06909001B2

Reaction notes

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