Hydrochloric Acid → HCID 19597498, compound

HRID 611542Notes

Reaction equation

HRID 611542 reaction equation
Cl.[O:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([CH:25]3[CH2:30][O:29]C(C4C=CC=CC=4)[O:27][CH2:26]3)[CH:16]=2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)CC>CO>[NH2:24][C:22]1[C:23]2[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)=[CH:10][CH:11]=3)=[CH:16][N:17]([CH:25]([CH2:26][OH:27])[CH2:30][OH:29])[C:18]=2[N:19]=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 19597522HCID 19597522, compound

Product 1

HCID 19597498HCID 19597498, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dilute hydrochloric acid (45 ml of 2M solution) was added to 5-(4-phenoxyphenyl)-7-(2-phenyl-1,3-dioxan-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (170 mg) and the mixture heated to boiling under reflux. Propan-1-ol (30 ml) was added and the mixture boiled under reflux for 6 hours and then the propanol was distilled off. The mixture was evaporated under reduced pressure to give a residue which was triturated with ethyl acetate and then filtered to give a solid which was dissolved in methanol, and purified by chromatography to give 2-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]propan-1,3-diol. The structure was confirmed by 1H nmr and mass spectra.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux
  3. temperatureunder reflux for 6 hours
  4. distillationthe propanol was distilled off
  5. customThe mixture was evaporated under reduced pressure
  6. customto give a residue which
  7. customwas triturated with ethyl acetate
  8. filtrationfiltered
  9. customto give a solid which
  10. custompurified by chromatography

Sources & evidence

ORD record
ord-87c4358e042e453ea593b2008e1474ef
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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