Potassium Carbonate → HCID 69284611, compound

HRID 2200514Notes

Reaction equation

HRID 2200514 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[N:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:12]1[CH:11]=[C:10]([NH2:9])[CH:15]=[N:14][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 783452-BromopyrimidineHCID 53398527(5-Aminopyridin-3-yl)boronic acid hydrochloride

Product 1

HCID 69284611HCID 69284611, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

The mixture of 2-bromopyrimidine (0.76 g, 4.80 mmol), (5-aminopyridin-3-yl)boronic acid hydrochloride (1.00 g, 5.75 mmol), Pd(Ph3P)2Cl2 (0.73 g, 0.96 mmol) and K2CO3 (2.78 g, 20.2 mmol) in dioxane (40 mL) and water (10 mL) was degassed with argon stream. It was stirred at 95° C. in argon atmosphere for overnight. The mixture was concentrated in vacuo to dryness. The solid was triturated with dioxane and EtOAc. The organic solutions were combined, filtered, concentrated and subjected to flash column (0-8% MeOH in DCM) to isolate 5-(pyrimidin-2-yl)pyridin-3-amine (0.24 g).

Workup

  1. customwas degassed with argon stream
  2. concentrationThe mixture was concentrated in vacuo to dryness
  3. customThe solid was triturated with dioxane and EtOAc
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e2238ca1fa14493395a02ba039450726
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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