2-Aminopyridine → 4-(2-chloro-4-pyrimidinyl)-N-(3-fluorophenyl)-2-pyridinamine

HRID 913298Notes

Reaction equation

HRID 913298 reaction equation
N1C=CC=CC=1N.[F:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](NCC(OC)C)[N:23]=3)[CH:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1.[Cl:34]C1N=C(Cl)C=CN=1>O1CCOCC1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:34][C:24]1[N:23]=[C:22]([C:20]2[CH:19]=[CH:18][N:17]=[C:16]([NH:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[CH:10]=3)[CH:21]=2)[CH:27]=[CH:26][N:25]=1

Participants

7

Reactant 3

HCID 104392-AminopyridineHCID 775312,4-DichloropyrimidineHCID 673888874-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-(2-methoxypropyl)-2-pyrimidinamine

Product 1

HCID 866467814-(2-chloro-4-pyrimidinyl)-N-(3-fluorophenyl)-2-pyridinamine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-fluorophenyl)-4-trimethylstannyl)-2-pyridinamine (i.e., the product of Step B) (4.0 g, 11 mmol) in 1,4-dioxane (100 mL) under nitrogen was added 2,4-dichloropyrimidine (2.26 g, 15 mmol), copper iodide (216 mg, 1.1 mmol) and bis(triphenylphosphine)palladium(II) dichloride (400 mg, 0.57 mmol). The resulting mixture was stirred at reflux for 4 h. After cooling to room temperature, the solution was concentrated under reduced pressure. The resulting residue was purified using column chromatography on silica gel eluted with 25% ethyl acetate in hexanes to afford 2.3 g of title compound as a yellow solid.

Workup

  1. temperatureat reflux for 4 h
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe resulting residue was purified
  4. washeluted with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-97072ad918f74c008d693c55654a9fbf
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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