HCID 70205596, compound → HCID 54559729, compound

HRID 362304Notes

Reaction equation

HRID 362304 reaction equation
[C:1]1([C:7]2[C:15]3[C:14]([NH2:16])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23]CC4C=CC=CC=4)[CH:18]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].C1COCC1>[C:1]1([C:7]2[C:15]3[C:14]([NH2:16])=[N:13][CH:12]=[N:11][C:10]=3[N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 70205596HCID 70205596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54559729HCID 54559729, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.61 g of 5-phenyl-7-(3-benzyloxyphenyl)-4-aminopyrrolo[2,3-d]pyrimidine (Ex. 11) and 1.0 g of palladium on carbon 10% are stirred at 40° C. for 30 h in 100 ml of THF until the amount of hydrogen theoretically required has been consumed. After cooling to RT, the mixture is filtered and the filtrate is concentrated in an RE. The residue is slurried with ether and the crystals are filtered off. Recrystallization from methylene chloride/ethanol and from chloroform does not give a pure product. After chromatography on silica gel (methylene chloride/methanol containing NH3 (4N) 92:8), the product-containing fractions are concentrated. The residue is dissolved in hot chloroform, the solution is cooled to 0° C. and the crystals are filtered off. After filtration and drying under HV, pure 5-phenyl-7-(3-hydroxyphenyl)-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 227°-228° C. is obtained. 1H--NMR (d6 -DMSO): delta (ppm)=6.2 (br. s, 2H), 6.8 (br. d, 1H), 7.2-7.4 (m, 4H), 7.5-7.6 (m, 4H), 7.7 (s, 1H), 8.2 (s, 1H), 9.8 (s, 1H).

Workup

  1. customtheoretically required has been consumed
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated in an RE
  4. filtrationthe crystals are filtered off
  5. customRecrystallization from methylene chloride/ethanol
  6. customfrom chloroform does not give a pure product
  7. concentrationAfter chromatography on silica gel (methylene chloride/methanol containing NH3 (4N) 92:8), the product-containing fractions are concentrated
  8. dissolutionThe residue is dissolved in hot chloroform
  9. temperaturethe solution is cooled to 0° C.
  10. filtrationthe crystals are filtered off
  11. filtrationAfter filtration
  12. dry with materialdrying under HV, pure 5-phenyl-7-(3-hydroxyphenyl)-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 227°-228° C.
  13. customis obtained

Sources & evidence

ORD record
ord-81d1accda48d4a15b40fe7624a4307e7
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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