4-tert-Butylbenzaldehyde → HCID 178440764, compound

HRID 729354Notes

Reaction equation

HRID 729354 reaction equation
[N:1]1[CH:6]=[C:5]([NH2:7])[C:4]([NH2:8])=[C:3]([NH2:9])[CH:2]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11]>C(O)(C)C.[Pd]>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([C:18]2[NH:8][C:4]3[C:5]([NH2:7])=[CH:6][N:1]=[CH:2][C:3]=3[N:9]=2)=[CH:20][CH:21]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 703244-tert-ButylbenzaldehydeHCID 419566Pyridine-3,4,5-triamine

Product 1

HCID 178440764HCID 178440764, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Pyridine-3,4,5-triamine 3 (100 mg, 0.81 mmol) was dissolved in isopropanol (4 ml) with Pd/C (20 mg of 10% powder). 4-t-butyl benzaldehyde (150 mg, 0.92 mmol) was added, and this mixture was refluxed for 48 hours. The reaction mixture was filtered through CELITE to remove the palladium, and the crude was purified by HPLC (Method E) to yield the title compound 4 (81 mg (37%), 0.3 mmol). 1H NMR (DMSO-d6): δ 8.64 (bs, 1H), 8.18 (d, J=8.6 Hz, 2H), 7.75 (s,1H), 7.69 (d, J=8.6 Hz, 2H), 6.30-6.61 (bs, 2H), 1.35 (s, 9H). MS (ESI-POS): [M+H]+=266.

Workup

  1. temperaturethis mixture was refluxed for 48 hours
  2. filtrationThe reaction mixture was filtered through CELITE
  3. customto remove the palladium
  4. customthe crude was purified by HPLC (Method E)

Sources & evidence

ORD record
ord-953c17d99bb14da29c8767d6611b3706
Source dataset
uspto-grants-2009_09
Patent number
US07582634B2

Reaction notes

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