HCID 178463595, compound → HCID 178463591, compound

HRID 1976561Notes

Reaction equation

HRID 1976561 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[CH2:13][N:14]1[C:22]2[C:18]([N:19]=[C:20]([C:23]([O:26]CC3C=CC=CC=3)([CH3:25])[CH3:24])[N:21]=2)=[C:17]([NH:34][CH2:35][CH3:36])[N:16]=[CH:15]1)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[ClH:1].[CH2:35]([NH:34][C:17]1[N:16]=[CH:15][N:14]([CH2:13][C:12]2[CH:37]=[CH:38][C:39]([O:40][CH3:41])=[C:10]([OH:9])[CH:11]=2)[C:22]2[C:18]=1[N:19]=[C:20]([C:23]([OH:26])([CH3:25])[CH3:24])[N:21]=2)[CH3:36]

Participants

4

Reactant 1

HCID 178463595HCID 178463595, compound

Product 1

HCID 178463591HCID 178463591, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The above crude 3-(3-benzyloxy-4-methoxy-benzyl)-8-(1-benzyloxy-1-methyl-ethyl)-6-ethylamino-3H-purine hydrochloride (3.28 g, 5.7 mmole) was hydrogenated at room temperature and pressure in a mixture of THF:methanol 1:1 (60 ml) with 10% Pd-C (0.66 g). The catalyst was filtered off, the solvents evaporated in vacuo and the residue crystallized from acetone to give 6-ethylamino-3-(3-hydroxy-4-methoxy-benzyl)-8-(1-hydroxy-1-methyl-ethyl)-3H-purine hydrochloride (1.80 g, 80.0%), mp 184-185° C.

Workup

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

Sources & evidence

ORD record
ord-2a690ad211a34b3484f964e116472068
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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