Ammonium formate → HCID 178419948, compound

HRID 2289489Notes

Reaction equation

HRID 2289489 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[N:16]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([N:23]5[CH2:28][CH2:27][N:26](C(OCC6C=CC=CC=6)=O)[CH2:25][CH2:24]5)=[N:21][CH:22]=4)[CH:14]=[CH:13][N:12]=3)=[CH:9][C:4]=2[N:3]=[N:2]1.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[N:16]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([N:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)=[N:21][CH:22]=4)[CH:14]=[CH:13][N:12]=3)=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178525151HCID 178525151, compound

Product 1

HCID 178419948HCID 178419948, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of N-(5-benzotriazolyl)-4-(2-(4-benzyloxycarbonylpiperazin-1-yl) pyrid-5-yl)-2-pyrimidineamine (200 mg, 0.39 mmol) and ammonium formate (400 mg, 6.35 mmol) in glacial acetic acid (5 ml) was treated with 10% palladium on charcoal (50 mg) and stirred for 24 h at room temperature. The mixture was filtered through Celite® washing with methanol, then evaporated and the residue subjected to column chromatography (silica, 0.88 ammonia-methanol-dichloromethane, 2:10:88) to afford the title compound (70 mg) as a white solid m.p. 280-283°. δH (d6DMSO) 2.79 (4H, m), 3.57 (4H, m), 6.92 (1H, d, J 9.1 Hz), 7.37 (1H, d, J 5.3 Hz), 7.59 (1H, d, J 9.1 Hz), 7.85 (1H, d, J 9.1 Hz), 8.27 (1H, m), 8.48 (1H, d, J 5.3 Hz), 8.57 (1H, s), 8.96 (1H, s) and 9.86 (1H, s).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashing with methanol
  3. customevaporated

Sources & evidence

ORD record
ord-d4d3d9ffd55443caba9c521e6dec08ab
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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