HCID 68156882, compound → HCID 68157528, compound

HRID 243162Notes

Reaction equation

HRID 243162 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:7]=1>[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:10]=[CH:11][CH:12]=[CH:13][N:14]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68156882HCID 68156882, compound

Product 1

HCID 68157528HCID 68157528, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(5-Fluoro-2-nitrophenyl)pyrimidin-2-yl-amine (336 mg, 1.43 mmol) in IMS (25.0 ml) was added to palladium on charcoal (10 wt %, 35.0 mg) and stirred under a hydrogen atmosphere overnight. The mixture was filtered through Celite® and the filtrate concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% methanol/DCM) to yield the title compound (215 mg, 1.05 mmol, 74%). 1H NMR (MeOD, 400 MHz): δ 8.37 (2H, d, J=4.9 Hz), 7.29 (1H, dd, J 10.4, 2.9 Hz), 6.84 (1H, dd, J 8.8, 5.6 Hz), 6.77 (1H, t, J=4.9 Hz), 6.72 (1H, ddd, J 8.6, 8.1, 2.9 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by chromatography (SiO2, 0-10% methanol/DCM)

Sources & evidence

ORD record
ord-2803f3ac28ed49e3ada509edbb1ad4a1
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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