5-(3-Benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine → 5-(3-Hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine

HRID 362313Notes

Reaction equation

HRID 362313 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)[CH:26]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 702056565-(3-Benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 545259215-(3-Hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.35 g of 5-(3-benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine are hydrogenated in a hydrogen atmosphere at normal pressure and about 40° C. for 16 h in 30 ml of methanol in the presence of 0.3 g of 5% palladium/carbon. After filtration through Celite, the solvent is stripped off and the residue is slurried in ether, filtered, slurried again in EA, filtered and dried. 5-(3-Hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an m.p. of 120°-122° C. is obtained.

Workup

  1. filtrationAfter filtration through Celite
  2. filtrationfiltered
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-479d26130e0940119c2f44d688f2a8a3
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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