HCID 53695335, compound → 5-(3-Hydroxyphenyl)-7-[4-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo-[2,3-d]pyrimidine

HRID 362314Notes

Reaction equation

HRID 362314 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][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH:38]=[CH:37][N:36]=[CH:35]4)=[CH:27][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:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH:38]=[CH:37][N:36]=[CH:35]4)=[CH:29][CH:30]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 53695335HCID 53695335, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 544664905-(3-Hydroxyphenyl)-7-[4-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo-[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.7 g of 5-(3-benzyloxyphenyl)-7-[4-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine are hydrogenated in a hydrogen atmosphere at normal pressure and about 40° C. for 24 h in 40 ml of methanol in the presence of 0.4 g of 5% palladium/carbon. After filtration through Celite and chromatography on silica gel (methylene chloride/methanol containing 5% of about 5N ammonia in methanol 9:1), 5-(3-hydroxyphenyl)-7-[4-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an m.p. of 221°-223° C. is obtained.

Workup

  1. filtrationAfter filtration through Celite and chromatography on silica gel (methylene chloride/methanol containing 5% of about 5N ammonia in methanol 9:1), 5-(3-hydroxyphenyl)-7-[4-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine having an m.p. of 221°-223° C.
  2. customis obtained

Sources & evidence

ORD record
ord-073ed2f01b6d455cb522ad8d17f5c279
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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