Iodine → 6-Bromo-3-iodopyrazolo[1,5-a]pyrimidine

HRID 1255862Notes

Reaction equation

HRID 1255862 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.[I:11]I>C(#N)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[I:11])[CH:7]=1

Participants

4

Reactant 2

HCID 807IodineHCID 222367016-Bromopyrazolo[1,5-a]pyrimidine

Product 1

HCID 568452436-Bromo-3-iodopyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of compound 6-bromopyrazolo[1,5-a]pyrimidine (1 eq), ceric ammonium nitrate (0.6 eq), and I2 (0.6 eq) in acetonitrile (10 mL) was stirred over a period of 24 h at room temperature. The formed precipitate was filtered off, washed with acetonitrile, and recrystallized from acetonitrile. The filtrate was evaporated, and the product was extracted with dichloromethane. The latter was evaporated, and the residue was recrystallized from acetonitrile to give 6-bromo-3-iodopyrazolo[1,5-a]pyrimidine.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. washwashed with acetonitrile
  3. customrecrystallized from acetonitrile
  4. customThe filtrate was evaporated
  5. extractionthe product was extracted with dichloromethane
  6. customThe latter was evaporated
  7. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-fbf98b2bcc1e45488a6c9440734e81bf
Source dataset
uspto-grants-2013_06
Patent number
US08461162B2

Reaction notes

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