Sodium ethoxide → 3-Butyl-8-chloro-1-{3-[3-(2-chlorobenzyl)-1,2,4-oxadiazol-5-yl]propyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097658Notes

Reaction equation

HRID 1097658 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=O)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32]/[C:33](=[N:36]/[H])/[NH:34]O.[O-]CC.[Na+]>CCO>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][C:19]2[O:21][N:36]=[C:33]([CH2:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Cl:25])[N:34]=2)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 59395861Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoateHCID 178506458HCID 178506458, compound

Product 1

HCID 593958473-Butyl-8-chloro-1-{3-[3-(2-chlorobenzyl)-1,2,4-oxadiazol-5-yl]propyl}-3,7-dihydro-1H-purine-2,6-dioneYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (53 mg, 0.15 mmol) and (1Z)-2-(2-chlorophenyl)-N-hydroxyethanimidamide (30 mg, 0.18 mmol; Entry 1, table 7) were heated in EtOH (0.75 ml) with 21% ethanolic sodium ethoxide (0.083 ml, 0.22 mmol) at 140° C. for 10 min. The mixture was then partitioned between EtOAc and 2M HCl and the organic phase evaporated. The product was purified by MDAP to yield the title compound as a solid (34.8 mg).

Workup

  1. customThe mixture was then partitioned between EtOAc and 2M HCl
  2. customthe organic phase evaporated
  3. customThe product was purified by MDAP

Sources & evidence

ORD record
ord-4e8ffc09fcc34ac092a883db753a0753
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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