Sodium Hydroxide → 8-(4-Aminobenzyl)-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione

HRID 858051Notes

Reaction equation

HRID 858051 reaction equation
Cl.[NH2:2][C:3]1[N:8]([CH3:9])[C:7](=[O:10])[N:6]([CH3:11])[C:5](=[O:12])[C:4]=1[NH:13][C:14](=O)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[OH-].[Na+]>CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]2[NH:13][C:4]3[C:5](=[O:12])[N:6]([CH3:11])[C:7](=[O:10])[N:8]([CH3:9])[C:3]=3[N:2]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69115132HCID 69115132, compound

Product 1

HCID 2252288-(4-Aminobenzyl)-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of crude N-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-(4-amino-phenyl)-acetamide hydrochloride salt (0.68 mmol) in methanol (35 mL) was added 10% w/v aqueous sodium hydroxide (3.4 mL) and the mixture heated to 50° C. for 7 hrs. The reaction mixture was concentrated in vacuo to dryness and the residue triturated with warm tetrahydrofuran and filtered to remove insoluble inorganic material. The filtrate was concentrated in vacuo to give crude 8-(4-amino-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione which was of sufficient purity for subsequent use without additional purification (58%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. customthe residue triturated with warm tetrahydrofuran
  3. filtrationfiltered
  4. customto remove insoluble inorganic material
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-27bff9be5ce646e98bbb660f27a32969
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

Loading…