1,5-Dibromopentane → 2-Amino-5-piperidinomethylpyrrolo[2,3-d]pyrimidin-4-one

HRID 1903312Notes

Reaction equation

HRID 1903312 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.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][N:12]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:5]2[C:4](=[O:13])[N:3]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 202463772-Amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one

Product 1

HCID 204685472-Amino-5-piperidinomethylpyrrolo[2,3-d]pyrimidin-4-oneYield 30.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 4.5 ml of methanol were dissolved 151 mg of 2-amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one (dihydrochloride) and 138 mg of 1,5-dibromopentane, followed by addition of 2.4 ml of 1 N-sodium hydroxide. The mixture was stirred at room temperature for 4 days. The solvent was then distilled off under pressure and the residue was purified by silica gel column chromatography. The fractions containing the desired compound were pooled and after addition of an excess of hydrogen chloride/ethanol, concentrated to dryness, followed by precipitation with ether to give 45 mg of the desired compound.

Workup

  1. distillationThe solvent was then distilled off under pressure
  2. customthe residue was purified by silica gel column chromatography
  3. additionThe fractions containing the desired compound
  4. additionafter addition of an excess of hydrogen chloride/ethanol
  5. concentrationconcentrated to dryness
  6. customfollowed by precipitation with ether

Sources & evidence

ORD record
ord-0f71452bb0eb40b192ef1df5e3e0df32
Source dataset
uspto-grants-1984_03
Patent number
US04435569

Reaction notes

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