Water → HCID 118482856, compound

HRID 2208635Notes

Reaction equation

HRID 2208635 reaction equation
I[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][N:3]=1.[Cl:11][C:12]1[C:17]([F:18])=[CH:16][C:15](B2OC(CC)(CC)C(CC)(CC)O2)=[CH:14][N:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.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.C(OC)(C)(C)C>[Cl:11][C:12]1[N:13]=[CH:14][C:15]([C:2]2[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][N:3]=2)=[CH:16][C:17]=1[F:18]

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 90241557HCID 90241557, compoundHCID 118482857HCID 118482857, compound

Product 1

HCID 118482856HCID 118482856, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

65 mmol of 2-iodo-5-propylpyrimidine and 65 mmol of 2-chloro-3-fluoro-5-(4,4,5,5-tetraethyl-1,3,2-dioxaborolan-2-yl)pyridine are dissolved in 155 ml of dioxane, and 130 mmol of tripotassium phosphate and 2 mmol of tetrakis(triphenylphosphine)palladium catalyst are added. The mixture is heated at 100° C. for 17 hours with stirring. Water and methyl tert-butyl ether are added to the reaction solution, and the organic phase is washed with water, dried using sodium sulfate and evaporated. The residue is purified by chromatography on silica gel with dichloromethane/MTB ether 90/10, giving 2-(6-chloro-5-fluoropyridin-3-yl)-5-propylpyrimidine.

Workup

  1. washthe organic phase is washed with water
  2. customdried
  3. customevaporated
  4. customThe residue is purified by chromatography on silica gel with dichloromethane/MTB ether 90/10

Sources & evidence

ORD record
ord-2954a7787fe744cca6bedc2e2d774e9f
Source dataset
uspto-grants-2016_06
Patent number
US09376622B2

Reaction notes

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