Triethylamine → HCID 57961911, compound

HRID 541862Notes

Reaction equation

HRID 541862 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]([Cl: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>[Cl: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 86636274HCID 86636274, compound

Product 1

HCID 57961911HCID 57961911, compoundYield 37%

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}-2,5-dichloropyrimidin-4-amine dihydrochloride (50 mg, 0.12 mmol) and triethylamine (0.048 mL, 0.35 mmol) in a mixed solvent of 1,4-dioxane (0.80 mL) and N,N-dimethylformamide (0.80 mL) were added (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (8.0 mg, 0.014 mmol), palladium acetate (3.1 mg, 0.014 mmol) and cesium carbonate (75.2 mg, 0.23 mmol). The mixture was degassed by bubbling N2 through the solution. The sealed tube was then microwaved at 160° C. for 30 min. The reaction mixture was diluted with THF/MeOH, filtered and concentrated to give the residue, which was purified by silica gel column chromatography to provide the desired product as a white powder (14 mg, 37%). LCMS for C17H15ClN5 (M+H)+: m/z=324.0. 1H NMR (400 MHz, CD3OD): δ 8.70 (s, 1H), 8.02 (s, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.07 (m, 2H), 6.90 (dd, J=8.0, 1.6 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 6.79 (d, J=8.0 Hz, 1H), 3.22 (s, 4H).

Workup

  1. customThe mixture was degassed
  2. customby bubbling N2 through the solution
  3. customThe sealed tube was then microwaved at 160° C. for 30 min
  4. additionThe reaction mixture was diluted with THF/MeOH
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the residue, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ca68a1eb50445e59b56aa2818692217
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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