2-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine → 2-iso-Propylamino-4-[4-fluoro-phenylethynyl]pyrimidine

HRID 1645296Notes

Reaction equation

HRID 1645296 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1>C(N)(C)C.O>[CH:6]([NH:7][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1)([CH3:8])[CH3:5]

Participants

4

Reactant 1

HCID 121652312-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine

Product 1

HCID 121652372-iso-Propylamino-4-[4-fluoro-phenylethynyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6363IsopropylamineSolvent

Procedure

A solution of 2-chloro-4-(4-fluoro-phenylethynyl)-pyrimidine (1 equiv.) in iso-propylamine (0.2 M) is heated at 35° C. for 24 h. The mixture is cooled to rt, diluted with water, and extracted with EtOAc. The organic layer is concentrated and the residue purified by column chromatography to provide the title compound.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer is concentrated
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-38f8c25bb54641518de3f57b0fd9e272
Source dataset
uspto-grants-2012_02
Patent number
US08124765B2

Reaction notes

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