Methanol → HCID 178490828, compound

HRID 1976553Notes

Reaction equation

HRID 1976553 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][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([C:27]([O:30]CC1C=CC=CC=1)([CH3:29])[CH3:28])[N:7]=2.CO>C1COCC1.[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]([O:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([C:27]([OH:30])([CH3:28])[CH3:29])[N:7]=2

Participants

5

Reactant 2

HCID 887MethanolHCID 178490825HCID 178490825, compound

Product 1

HCID 178490828HCID 178490828, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-amino-8-(1-benzyloxy-1-methyl-ethyl)-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purine hydrochloride (2.13 g, 4.06 mmole), in THF:methanol,1:1 (60 ml), was hydrogenated at room temperature and pressure with 10% Pd-C (0.26 g) for 12 hours. The catalyst was filtered off and the solvents removed in vacuo. The residue was suspended in hot acetone, the solid collected at 0-5° C. (1.23 g) and recrystallized from methanol-acetone to give the title compound, 0.76 g (43.2%) mp 231-232° C.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe solvents removed in vacuo
  4. customthe solid collected at 0-5° C. (1.23 g)
  5. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-ea5f343d10d24ddeb419ad665212a400
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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