N-Iodosuccinimide → HCID 178494260, compound

HRID 473737Notes

Reaction equation

HRID 473737 reaction equation
[CH3:1][O:2][C:3]1[NH:4][CH:5]=[CH:6][C:7](=[O:9])[N:8]=1.C1C(=O)N([I:17])C(=O)C1>CN(C=O)C.O>[I:17][C:6]1[C:7](=[O:9])[N:8]=[C:3]([O:2][CH3:1])[NH:4][CH:5]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178494255HCID 178494255, compound

Product 1

HCID 178494260HCID 178494260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Methoxypyrimidin-4(1H)-one (1.00 g, 7.93 mmol) and n-iodosuccinimide (3.57 g, 15.86 mmol) were mixed in DMF (8 mL) under a nitrogen atmosphere. The reaction mixture was stirred at 70° C. for 2.5 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (3×). The combined organic layers were washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting solid was suspended in DCM, filtered, and washed with DCM to give 5-iodo-2-methoxypyrimidin-4(1H)-one. MS (ESI, pos. ion) m/z: 252.9 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with sat. sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfiltered
  8. washwashed with DCM

Sources & evidence

ORD record
ord-4c8fc64b5fef4392bfa67c51e5d1a98c
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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