Ethanol → 5-(4-Hydroxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine

HRID 362322Notes

Reaction equation

HRID 362322 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[C:24]3[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=3[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)[CH:27]=3)[CH:17]=2)=[CH:11][C:10]=1[CH3:40])C1C=CC=CC=1.[H][H].C(O)C>C1COCC1.[Pd]>[OH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[C:24]3[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=3[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][N:35]4[CH:39]=[CH:38][N:37]=[CH:36]4)[CH:27]=3)[CH:17]=2)=[CH:11][C:10]=1[CH3:40]

Participants

6

Reactant 3

HCID 702EthanolHCID 544738565-(4-Benzyloxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-amino-pyrrolo[2,3-d]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 543924415-(4-Hydroxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.35 g of 5-(4-benzyloxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-amino-pyrrolo[2,3-d]pyrimidine is hydrogenated in a hydrogen atmosphere at normal pressure and about 50° C. for 2 h in 15 ml of THF and 10 ml of ethanol in the presence of 0.2 g of 5% palladium/carbon. After filtration through Celite and chromatography on silica gel using methylene chloride/methanol 10:1, after crystallization from methylene chloride, 5-(4-hydroxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine having an m.p. of 150°-152° C. is obtained.

Workup

  1. filtrationAfter filtration through Celite and chromatography on silica gel
  2. customafter crystallization from methylene chloride, 5-(4-hydroxy-3,5-dimethylphenyl)-7-[3-(2-(1-imidazolyl)ethoxy)phenyl]-4-aminopyrrolo[2,3-d]-pyrimidine having an m.p. of 150°-152° C.
  3. customis obtained

Sources & evidence

ORD record
ord-15cf4fd5194844229521680a7b1b721a
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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