2-Bromopyridine → HCID 58973801, compound

HRID 2426279Notes

Reaction equation

HRID 2426279 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:6]=2[N:7]=1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 58973801HCID 58973801, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-chloro-7H-pyrrolo-[2,3-d]pyrimidine 3 (0.53 g, 3.5 mmol), 2-bromopyridine (0.66 mL, 1.1 g, 6.9 mmol), copper(I) iodide (0.20 g, 1.0 mmol), trans-1,2-diaminocyclohexane (0.12 mL, 0.1 Ig, 1.0 mmol), and potassium phosphate (2.2 g, 10 mmol) in 10 mL 1,4-dioxane is heated to 100° C. and stirred for four hours. The reaction mixture is cooled to room temperature, diluted with ethyl acetate, and washed with water and brine. The organic extract was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, Hexane : Ethyl acetate/5:1) provided 4 (0.69 g, 87%) as a white solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, Hexane : Ethyl acetate/5:1)

Sources & evidence

ORD record
ord-0a555b6d84214241adf12eecb702d9f2
Source dataset
uspto-grants-2011_06
Patent number
US07968557B2

Reaction notes

Loading…