4-Iodobenzaldehyde → 2-Amino-5-(p-iodobenzyl)aminomethylpyrrolo[2,3-d]pyrimidin-4-one

HRID 1903283Notes

Reaction equation

HRID 1903283 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[C:4](=[O:13])[N:3]=1.[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C[O-].[Na+].[BH4-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH:12][CH2:19][C:18]3[CH:21]=[CH:22][C:15]([I:14])=[CH:16][CH:17]=3)=[C:5]2[C:4](=[O:13])[N:3]=1

Participants

6

Reactant 4

HCID 966574-IodobenzaldehydeHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 202463772-Amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 204685712-Amino-5-(p-iodobenzyl)aminomethylpyrrolo[2,3-d]pyrimidin-4-oneYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 40 ml of dry methanol were suspended 126 mg of 2-amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one (dihydrochloride) and 116 mg of p-iodobenzaldehyde. After addition of 1 N methanolic sodium methoxide, the mixture was stirred at room temperature for 30 min. To this mixture was added 76 mg of sodium borohydride and the reaction was conducted at room temperature for 15 min. The reaction was then terminated by addition of 500 mg silica gel. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography to give 121 mg of the desired compound.

Workup

  1. waitthe reaction was conducted at room temperature for 15 min
  2. customThe reaction was then terminated by addition of 500 mg silica gel
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c036a8432ed64ce7bb8e831aa6ac3d50
Source dataset
uspto-grants-1984_03
Patent number
US04435570

Reaction notes

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