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

HRID 1097660Notes

Reaction equation

HRID 1097660 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:27]=[C:28]([CH2:33]/[C:34](=[N:37]/[H])/[NH:35]O)[CH:29]=[CH:30][C:31]=1[Cl:32].[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:35]=[C:34]([CH2:33][C:28]3[CH:29]=[CH:30][C:31]([Cl:32])=[C:26]([Cl:25])[CH:27]=3)[N:37]=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 178506462HCID 178506462, compound

Product 1

HCID 593957433-Butyl-8-chloro-1-(3-{3-[(3,4-dichlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3,7-dihydro-1H-purine-2,6-dioneYield 47.7%

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 (71 mg, 0.2 mmol), (1Z)-2-(3,4-dichlorophenyl)-N-hydroxyethanimidamide (48 mg, 0.22 mmol) and 21% by wt. ethanolic sodium ethoxide (0.111 ml, 0.3 mmol) were heated together in EtOH (1 ml) in the microwave reactor at 140° C. for 10 min. The mixture was then partitioned between EtOAc and 2M HCl, the organic phase separated and evaporated, and the crude product was purified by MDAP to give the title compound as a solid (48.8 mg).

Workup

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

Sources & evidence

ORD record
ord-142a45ee64b443d29df2b97712f10631
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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