N-Iodosuccinimide → HCID 59654182, compound

HRID 1784461Notes

Reaction equation

HRID 1784461 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:13]=[CH:12][CH:11]=[CH:10][N:6]2[C:7](=[O:9])[CH:8]=1.[I:14]N1C(=O)CCC1=O>C(#N)C>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:13]=[CH:12][CH:11]=[CH:10][N:6]2[C:7](=[O:9])[C:8]=1[I:14]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 51550272-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 59654182HCID 59654182, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 21.9 g (112.5 mmol) of the product from Step 1 (11) and 38.9 g (168.8 mmol) of N-iodosuccinimide in 660 mL of acetonitrile was stirred at 80° C. under nitrogen for 16 hours. The reaction mixture was then allowed to cool to ambient temperature and the acetonitrile was removed in vacuo. The resulting solid was washed with water, saturated Na2O3S2, saturated NaHCO3, and brine, and then filtered. Drying under reduced pressure at 40° C. overnight yielded 29.8 g (92.9 mmol, 83%) of 2-(chloromethyl)-3-iodo-4H-pyrido[1,2-a]pyrimidin-4-one (12) as a light brown solid.

Workup

  1. temperatureto cool to ambient temperature
  2. customthe acetonitrile was removed in vacuo
  3. washThe resulting solid was washed with water, saturated Na2O3S2, saturated NaHCO3, and brine
  4. filtrationfiltered
  5. customDrying under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-ad1e9031b79f410db9c8eca5f1bc3535
Source dataset
uspto-grants-2009_03
Patent number
US07504405B2

Reaction notes

Loading…