Hydrochloric Acid → 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzonitrile

HRID 2252764Notes

Reaction equation

HRID 2252764 reaction equation
O[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.P(Cl)(Cl)([Cl:22])=O>C(#N)C.O1CCOCC1>[Cl:22][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 178509549HCID 178509549, compound

Product 1

HCID 865953354-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

4-(4-Hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzonitrile (2.36 g, 0.01 mol) are suspended in 40 ml acetonitril and 4.99 ml (0.02 mol) 4 N hydrochloric acid solution in dioxane. After addition of 3.66 ml (0.04 mol) phosphorus oxichloride the mixture is heated under reflux for 3 days. The solid is filtered off and the mother liquor evaporated. The residue and the solid are dissolved in 30 ml DMF at 60° C. and 25 ml of a conc. sodium bicarbonate solution and 25 ml water are added and the resulting suspension cooled, filtered and the solid washed with water. The title compound is dried at 100° C. for 6 h under reduced pressure; m.p. 296-297° C.; HPLC tR=11.59 min.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 days
  3. filtrationThe solid is filtered off
  4. customthe mother liquor evaporated
  5. dissolutionThe residue and the solid are dissolved in 30 ml DMF at 60° C.
  6. addition25 ml of a conc. sodium bicarbonate solution and 25 ml water are added
  7. temperaturethe resulting suspension cooled
  8. filtrationfiltered
  9. washthe solid washed with water
  10. dry with materialThe title compound is dried at 100° C. for 6 h under reduced pressure

Sources & evidence

ORD record
ord-886a58520ec64bca96828a73ec6e4cc3
Source dataset
uspto-grants-2008_01
Patent number
US07323469B2

Reaction notes

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