HCID 178490822, compound → HCID 178490823, compound

HRID 1976566Notes

Reaction equation

HRID 1976566 reaction equation
[ClH:1].[NH2:2][C:3]1[N:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21]CC3C=CC=CC=3)[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([CH:29]([CH3:31])[CH3:30])[N:7]=2>C1COCC1.CO.[Pd]>[ClH:1].[NH2:2][C:3]1[N:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([CH:29]([CH3:31])[CH3:30])[N:7]=2

Participants

4

Reactant 1

HCID 178490822HCID 178490822, compound

Product 1

HCID 178490823HCID 178490823, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6-Amino-3-(3-benzyloxy-4-methoxy-benzyl)-8-isopropyl-3H-purine hydrochloride (4.04 g, 9.2 mmole), in THF:methanol (1:1) (600 ml) was hydrogenated for 10 hours over 10% Pd-C (0.8 g) at room temperature and pressure. The catalyst was filtered off, the solvents removed in vacuo and the residue crystallized from acetone to give 6-amino-3-(3-hydroxy-4-methoxy-benzyl)-8-isopropyl-3H-purine hydrochloride (2.53 g, 78.8%), mp 125-130/185-195° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvents removed in vacuo
  3. customthe residue crystallized from acetone

Sources & evidence

ORD record
ord-9851292e6fe64b7f88fdd5e45484398f
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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