HCID 66597624, compound → HCID 49819036, compound

HRID 2276293Notes

Reaction equation

HRID 2276293 reaction equation
[CH2:1]([C:3]1[N:4]([CH3:31])[C:5]2[C:10]([N:11]=1)=[C:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:8]=[C:7]([S:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([N+:28]([O-])=O)[CH:21]=1)[N:6]=2)[CH3:2]>ClCCl.CO.[Pd]>[NH2:28][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[O:26][CH3:27])[CH2:19][S:18][C:7]1[N:6]=[C:5]2[C:10]([N:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH3:31])=[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:8]=1

Participants

5

Reactant 1

HCID 66597624HCID 66597624, compound

Product 1

HCID 49819036HCID 49819036, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

8-ethyl-9-methyl-6-morpholino-2-(3-nitro-4-methoxybenzylsulfanyl)-9H-purine (4.10 g, 9.23 mmol) was dissolved in dichloromethane (50 ml) and methanol (50 ml), 1.0 g of Pd/C was added and catalytic hydrogenation was performed under normal pressure for 18 hours. Celite was used to filter off Pd/C, and the filtrate was distilled away under reduced pressure. Ether was added to the residue and the precipitated crystals were collected by filtration to obtain 2.74 g (72% yield) of 2-(3-amino-4-methoxybenzylsulfanyl)-8-ethyl-9-methyl-6-morpholino-9H-purine.

Workup

  1. filtrationto filter off Pd/C
  2. distillationthe filtrate was distilled away under reduced pressure
  3. additionEther was added to the residue
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-03e336f60fb4490190867e249bd65414
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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