Potassium Fluoride → HCID 57678406, compound

HRID 491501Notes

Reaction equation

HRID 491501 reaction equation
[I:1][C:2]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][Si](C)(C)C)=[CH:13][C:3]=1[O:4][C:5]1[C:6]([NH2:12])=[N:7][C:8]([NH2:11])=[N:9][CH:10]=1.[F-].[K+]>Br.CN(C=O)C.O.CCOC(C)=O.[NH4+].[OH-]>[C:17]([C:14]1[CH:15]=[CH:16][C:2]([I:1])=[C:3]([CH:13]=1)[O:4][C:5]1[C:6]([NH2:12])=[N:7][C:8]([NH2:11])=[N:9][CH:10]=1)#[CH:18]

Participants

8

Reactant 2

HCID 522689Potassium FluorideHCID 688390485-{2-Iodo-5-[(trimethylsilyl)ethynyl]phenoxy}pyrimidine-2,4-diamine

Product 1

HCID 57678406HCID 57678406, compoundYield 43.3%

Reagents, catalysts & solvents 5

HCID 260Hydrogen BromideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 5-(2-Iodo-5-trimethylsilanylethynyl-phenoxy)-pyrimidine-2,4-diamine (0.4 g, 2.36 mmol), potassium fluoride (41 mg, 7.07 mmol) and HBr (2 drops of 48% aqueous solution) in DMF was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and EtOAc and basified with 1 mL NH4OH. The organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (4% MeOH in CH2Cl2 with 0.1% NH4OH) to give 0.36 g of 5-(5-Ethynyl-2-iodo-phenoxy)-pyrimidine-2,4-diamine, MP=156-159° C., MS (M+H)=352.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica (4% MeOH in CH2Cl2 with 0.1% NH4OH)

Sources & evidence

ORD record
ord-3ccbf3e8520040ed90d869984032ce71
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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