N-Iodosuccinimide → 2,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

HRID 529638Notes

Reaction equation

HRID 529638 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[C:10]([I:12])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574159022,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
16 °C

Procedure

A 50-L jacketed reactor was charged with 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (950 g, 5053 mmol) and DCM (16 L). The resulting tan suspension was cooled to 16° C., and N-iodosuccinimide (1598 g, 7104 mmol) was added portionwise over 20 min. The reaction mixture was stirred at room temperature for 16 h, after which time TLC analysis (2:1 hexanes/ethyl acetate) indicated complete reaction. The resulting precipitate was filtered, washed with DCM (3×1.5 L), and dried under reduced pressure at 40° C. for 64 h to afford 1447 g (Yield: 91%) of target compound as a beige solid. MS (ESI) m/z 314.0 [M+1]+.

Workup

  1. customreaction
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with DCM (3×1.5 L)
  4. customdried under reduced pressure at 40° C. for 64 h
  5. customto afford 1447 g (Yield: 91%) of target compound as a beige solid

Sources & evidence

ORD record
ord-34e894a6033343bda095392334b6eb69
Source dataset
uspto-grants-2016_05
Patent number
US09346812B2

Reaction notes

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