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

HRID 2408476Notes

Reaction equation

HRID 2408476 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[C:9]=1I.[C:18]([Cu])#[N:19]>CN(C=O)C>[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[C:18]#[N:19]

Participants

4

Reactant 2

HCID 674703526-(2-fluorophenyl)-7-iodo-5H-pyrrolo[3,2-d]pyrimidineHCID 178418546HCID 178418546, compound

Product 1

HCID 674703166-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(2-fluorophenyl)-7-iodo-5H-pyrrolo[3,2-d]pyrimidine and CuCN in DMF were heated for 30 min at 175° C. in a microwave vial. The reaction mixture was filtered through a metal scavenging resin column, rinsed with DMF (˜10 mL), and purified by HPLC (10-75% MeCN/H2O with 1% formic acid) to give 29 mg of desired (17% yield). LC-MS calculated for C13H7FN4: 238.2, found 239.09 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a metal
  2. washrinsed with DMF (˜10 mL)
  3. custompurified by HPLC (10-75% MeCN/H2O with 1% formic acid)
  4. customto give 29 mg

Sources & evidence

ORD record
ord-7599ed02326140438021c5105fa770a4
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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