2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide → N-(5-amino-2-(2,6-dimethylpyrimidin-4-ylamino)pyridine-4-yl)-2,6-dichlorobenzamide

HRID 449903Notes

Reaction equation

HRID 449903 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([NH:16][C:17]2[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([CH3:24])[N:18]=2)[CH:8]=1)=[O:5]>C(O)C.[Pd]>[NH2:13][C:12]1[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([Cl:1])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:29])=[CH:8][C:9]([NH:16][C:17]2[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([CH3:24])[N:18]=2)=[N:10][CH:11]=1

Participants

4

Reactant 1

HCID 671286552,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide

Product 1

HCID 59618403N-(5-amino-2-(2,6-dimethylpyrimidin-4-ylamino)pyridine-4-yl)-2,6-dichlorobenzamideYield 18.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide (0.057 g, 0.13 mmol) in dry ethanol (8 mL) was added palladium (0.015 g, 0.14 mmol) (10% on activated carbon powder, 50% water wet) in one portion at room temperature under N2. The resulting mixture was stirred under H2 balloon for 60 mins The mixture was filtered with Celite and the filtrate was concentrated by vacuum. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product (9.8 mg, yield: 18%). 1H NMR (DMSO-d6, 400 MHz): δ 10.2 (d, J=24.6 Hz, 1H), 9.58 (s, 1H), 8.17 (d, J=28.7 Hz, 1H), 7.85 (s, 1H), 7.59 (s, 3H), 7.08 (s, 1H), 4.81 (s, 2H), 2.38 (s, 3H), 2.25 (s, 3H). LCMS (ESI) m/z: 403.0 [M+H+].

Workup

  1. filtrationwas filtered with Celite
  2. concentrationthe filtrate was concentrated by vacuum
  3. customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

Sources & evidence

ORD record
ord-9f423e68e4004583bb0b75024882f580
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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