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

HRID 362315Notes

Reaction equation

HRID 362315 reaction equation
C([O:8][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]([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:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([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:13][CH:14]=1

Participants

5

Reactant 2

HCID 544421105-(4-Benzyloxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 543063155-(4-Hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-aminopyrrolo-[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.9 g of 5-(4-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 20 h in 40 ml of THF in the presence of 0.15 g of 10% palladium/carbon. After filtration through Celite and chromatography of the residue on silica gel (methylene chloride/methanol 9:1) 5-(4-hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-amino-pyrrolo[2,3-d]pyrimidine (Rf=0.2 silica gel, methylene chloride/methanol 9:1) is obtained.

Workup

  1. filtrationAfter filtration through Celite and chromatography of the residue on silica gel (methylene chloride/methanol 9:1) 5-(4-hydroxyphenyl)-7-[3-(3-(1-imidazolyl)propoxy)phenyl]-4-amino-pyrrolo[2,3-d]pyrimidine (Rf=0.2 silica gel, methylene chloride/methanol 9:1)
  2. customis obtained

Sources & evidence

ORD record
ord-b552b2d49cda4479b4b0595f55e49ffb
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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