4-tert-Butylbenzaldehyde → HCID 178440764, compound

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

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.