N-Iodosuccinimide → 6-Chloro-5-iodopyrimidin-4-amine

HRID 527986Notes

Reaction equation

HRID 527986 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[I:9]N1C(=O)CCC1=O>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9]

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 468558336-Chloro-5-iodopyrimidin-4-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloropyrimidin-4-amine (1 g, 7.8 mmol) in 5 mL N,N-dimethylformamide was added N-iodosuccinimide (2.6 g, 11.6 mmol) and the mixture subjected to microwave irradiation (Biotage Initiator) at 100° C. for 30 minutes. The mixture was diluted with water and ethyl acetate and the ethyl acetate layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 25% ethyl acetate in hexane) afforded the title compound. LCMS: 255.91 (M+1)+.

Workup

  1. customthe mixture subjected to microwave irradiation (Biotage Initiator) at 100° C. for 30 minutes
  2. washthe ethyl acetate layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b694db7943114eb19921b039e6774af2
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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