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

HRID 1097662Notes

Reaction equation

HRID 1097662 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]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[CH2:33]/[C:34](=[N:37]/[H])/[NH:35]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:35]=[C:34]([CH2:33][C:27]3[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=3[Cl:25])[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 178506463HCID 178506463, compound

Product 1

HCID 593955373-Butyl-8-chloro-1-(3-{3-[(2-chloro-4-fluorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3,7-dihydro-1H-purine-2,6-dioneYield 52.6%

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 (100 mg, 0.28 mmol) and (1Z)-2-(2-chloro-4-fluorophenyl)-N-hydroxyethanimidamide (62.4 mg, 0.308 mmol) and 21% by wt. ethanolic sodium ethoxide (0.157 ml, 0.42 mmol) were heated together in a microwave reactor in EtOH (1.5 ml) at 140° C. for 10 min. The mixture was worked up by partitioning between EtOAc and 2M HCl. The organic phase was evaporated and purified by MDAP to afford the title compound as a solid (73 mg).

Workup

  1. customby partitioning between EtOAc and 2M HCl
  2. customThe organic phase was evaporated
  3. custompurified by MDAP

Sources & evidence

ORD record
ord-6100f8b0d51c4bee8781ad1a5e9ee8aa
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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