N-Iodosuccinimide → 3-iodopyrazolo[1,5-c]pyrimidin-5(4H)-one

HRID 474319Notes

Reaction equation

HRID 474319 reaction equation
[N:1]1[N:5]2[CH:6]=[N:7][C:8](=[O:10])[CH2:9][C:4]2=[CH:3][CH:2]=1.[I:11]N1C(=O)CCC1=O>CN(C=O)C>[I:11][C:3]1[CH:2]=[N:1][N:5]2[C:4]=1[CH2:9][C:8](=[O:10])[N:7]=[CH:6]2

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66676395pyrazolo[1,5-c]pyrimidin-5(4H)-one

Product 1

HCID 666774913-iodopyrazolo[1,5-c]pyrimidin-5(4H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrazolo[1,5-c]pyrimidin-5(4H)-one (1.0 g, 7.4 mM, 1.0 equiv) and N-iodosuccinimide (1.67 g, 7.4 mM, 1.0 equiv) were combined with 20 mL of DMF and warmed slightly. Within minutes a heavy precipitate formed. The reaction mixture was stirred an additional 1 h at ambient temperature then cooled on an icewater bath and filtered. The collected solid was washed with 20 mL of dichloromethane and air dried to give 1.66 g (86%) of 3-iodopyrazolo[1,5-c]pyrimidin-5(4H)-one. LCMS (ESI) m+H=262.2; 1H NMR (400 MHz, DMSO-d6) δ: 12.1 (s, 1H), 8.5 (d, 1H, J=7.6), 7.84 (s, 1H), 6.01 (d, 1H, J=7.1).

Workup

  1. temperaturewarmed slightly
  2. customWithin minutes a heavy precipitate formed
  3. temperaturethen cooled on an icewater bath
  4. filtrationfiltered
  5. washThe collected solid was washed with 20 mL of dichloromethane and air
  6. customdried

Sources & evidence

ORD record
ord-a08443e7cc0b448a9cc1a066d48f8e00
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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