Diiodomethane → HCID 22133807, compound

HRID 1369378Notes

Reaction equation

HRID 1369378 reaction equation
N[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[N:8]2[C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[C:4]([Cl:26])[N:3]=1.N(OCCC(C)C)=O.[I:35]CI>O1CCCC1>[Cl:26][C:4]1[N:3]=[C:2]([I:35])[N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[N:8]2[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 22133754HCID 22133754, compound

Product 1

HCID 22133807HCID 22133807, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[2-Amino-6-chloro-8-(3-fluorophenyl)-9H-9-purinyl]-benzonitrile (2.6 g) was dissolved in 105 ml of tetrahydrofuran, then 2.9 ml of isoamyl nitrite, 5.8 ml of diiodomethane and 1.37 g of cuprous iodide were added thereto and the mixture was heated under reflux for 1 hour. After the resulting mixture was cooled to room temperature, it was filtered to remove unnecessary substances and washed with 100 ml of ethyl acetate. The filtrate was concentrated to dryness and purified by a silica gel column (50 g of silica gel). It was eluted with ethyl acetate and hexane (1:1). The fractions containing the aimed product were collected, concentrated and suspended in 100 ml of a mixed solvent of ethyl acetate and hexane (1:4), and the resulting precipitates were collected by filtration to give 1.7 g of 3-[6-chloro-8-(3-fluorophenyl)-2-iodo-9H-9-purinyl]benzonitrile. The yield was 50%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationit was filtered
  4. customto remove unnecessary substances
  5. washwashed with 100 ml of ethyl acetate
  6. concentrationThe filtrate was concentrated to dryness
  7. custompurified by a silica gel column (50 g of silica gel)
  8. washIt was eluted with ethyl acetate and hexane (1:1)
  9. additionThe fractions containing the aimed product
  10. customwere collected
  11. concentrationconcentrated
  12. customthe resulting precipitates
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-672a3e7839cb4d19843dd66984872e5c
Source dataset
uspto-grants-2003_06
Patent number
US06579868B1

Reaction notes

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