2-(Tributylstannyl)pyrimidine → HCID 86685631, compound

HRID 2200516Notes

Reaction equation

HRID 2200516 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1)[NH2:5].C([Sn](CCCC)(CCCC)[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1.O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1)[NH2:5]

Participants

7

Reactant 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 86685632HCID 86685632, compound

Product 1

HCID 86685631HCID 86685631, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 3-bromo-5-(pyrimidin-2-yl)aniline (140 mg, 0.56 mmol),), 2-tributylstannylpyrimidine (420 mg, 1.12 mmol), Pd(Ph3P)4 (65 mg, 0.056 mmol) in 20 mL toluene and 5 mL dioxane was degassed with argon stream and stirred at 110° C. in argon atmosphere for two days. It was cooled to RT, diluted with EtOAc, filtered through celite, concentrated in vacuo, and subjected to silica flash column to isolate 3,5-di(pyrimidin-2-yl)aniline.

Workup

  1. temperatureIt was cooled to RT
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f718d1db532240d4bd44521d2904063f
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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