Triethylamine → HCID 57962324, compound

HRID 541865Notes

Reaction equation

HRID 541865 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([NH:18][C:19]3[C:24]([F:25])=[CH:23][N:22]=[C:21](Cl)[N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O.O1CCOCC1>[F:25][C:24]1[CH:23]=[N:22][C:21]2[NH:3][C:4]3[CH:5]=[CH:6][CH:7]=[C:8]([N:9]=3)[CH2:10][CH2:11][C:12]3[CH:13]=[C:14]([NH:18][C:19]=1[N:20]=2)[CH:15]=[CH:16][CH:17]=3

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86636275HCID 86636275, compound

Product 1

HCID 57962324HCID 57962324, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of N-{3-[2-(6-aminopyridin-2-yl)ethyl]phenyl}-2-chloro-5-fluoropyrimidin-4-amine dihydrochloride (35.0 mg, 0.084 mmol) and triethylamine (0.035 mL, 0.25 mmol) in a mixed solvent of 1,4-dioxane (0.70 mL) and N,N-dimethylformamide (0.70 mL) was added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.8 mg, 0.01 mmol), palladium acetate (2.3 mg, 0.01 mmol) and cesium carbonate (54.7 mg, 0.17 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 160° C. for 1 hour. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give a residue, which was purified by silica gel column chromatography to provide the desired product as a white powder (6.4 mg, 25%). LCMS for C17H15FN5 (M+H)+: m/z=308.1.

Workup

  1. customThe mixture was degassed
  2. customby bubbling N2 through the solution
  3. customThe sealed tube was then microwaved at 160° C. for 1 hour
  4. additionThe reaction mixture was diluted with THF/MeOH
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fe9e0394d2324b28820ef44412f762a1
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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