N-Iodosuccinimide → 6-(2-fluorophenyl)-7-iodo-5H-pyrrolo[3,2-d]pyrimidine

HRID 2408475Notes

Reaction equation

HRID 2408475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:15]2[CH:14]=[N:13][CH:12]=[N:11][C:10]=2[CH:9]=1.[I:17]N1C(=O)CCC1=O>CC(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:16][C:15]2[CH:14]=[N:13][CH:12]=[N:11][C:10]=2[C:9]=1[I:17]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 674703356-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 674703526-(2-fluorophenyl)-7-iodo-5H-pyrrolo[3,2-d]pyrimidineYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine (1.0 g) in acetone (25 mL) was added N-iodosuccinimide (1.4 g). The reaction was stirred at rt for 3 h, until complete conversion was observed by LC-MS. The reaction mixture was diluted with EtOAc (150 mL) and the solid was collected via filtration and washed with EtOAc yielding 1.23 g of desired (77% yield). LC-MS calculated for C12H7FIN3: 339.1, found 339.96 [M+].

Workup

  1. filtrationthe solid was collected via filtration
  2. washwashed with EtOAc yielding 1.23 g

Sources & evidence

ORD record
ord-78ca2239abcf45bfa31e5107466f4df5
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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