Benzyl Chloride → 2-Amino-5-dibenzylaminomethylpyrrolo[2,3-d]pyrimidin-4-one

HRID 1903314Notes

Reaction equation

HRID 1903314 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:5]2[C:4](=[O:20])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO.[I-].[Na+]>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][N:12]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:5]2[C:4](=[O:20])[N:3]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 204685402-Amino-5-benzylaminomethylpyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 202463722-Amino-5-dibenzylaminomethylpyrrolo[2,3-d]pyrimidin-4-oneYield 24.9%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In 30 ml of methanol was dissolved 172 mg of 2-amino-5-benzylaminomethylpyrrolo[2,3-d]pyrimidin-4-one (the compound of Example 4), followed by addition of 90 mg of anhydrous potassium carbonate, 2 mg of sodium iodide and 81 mg of benzyl chloride. The mixture was stirred on a water bath at 60° C. for 4 hrs. The solvent was then distilled off and the residue was purified by silica gel column chromatography to give 57 mg of the desired compound.

Workup

  1. distillationThe solvent was then distilled off
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-502030615bf548bc96bcac359d882794
Source dataset
uspto-grants-1984_03
Patent number
US04435569

Reaction notes

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