HCID 178490826, compound → HCID 178490829, compound

HRID 1976562Notes

Reaction equation

HRID 1976562 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]([C:29]([O:32]CC1C=CC=CC=1)([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]([C:29]([OH:32])([CH3:30])[CH3:31])[N:7]=2

Participants

4

Reactant 1

HCID 178490826HCID 178490826, compound

Product 1

HCID 178490829HCID 178490829, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of the above 6-amino-3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-3H-purine hydrochloride (3.22 g) in THF:methanol (1:1) (60 ml) was hydrogenated at room temperature and pressure for 2.5 hours with 10% Pd-C (0.64 g). The catalyst was filtered off and the solution evaporated to dryness in vacuo. The residue was crystallized from acetone to give 6-amino-3-(3-hydroxy-4-methoxy-benzyl)-8-(1-hydroxy-1-methyl-ethyl)-3H-purine hydrochloride, (1.67 g, 77.3%) mp 155-160° C.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe solution evaporated to dryness in vacuo
  4. customThe residue was crystallized from acetone

Sources & evidence

ORD record
ord-c004834fde6649989afe394aaff1d68e
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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