N'-Hydroxybenzenecarboximidamide → 3-Butyl-8-chloro-1-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)butyl]-3,7-dihydro-1H-purine-2,6-dione

HRID 1097700Notes

Reaction equation

HRID 1097700 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][CH2:19][C:20]([O:22]CC)=O)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].[C:26](=[N:34]O)([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[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][CH2:19][C:20]2[O:22][N:34]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:33]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 69186N'-HydroxybenzenecarboximidamideHCID 2723922Sodium ethoxideHCID 59395413ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate

Product 1

HCID 593954823-Butyl-8-chloro-1-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)butyl]-3,7-dihydro-1H-purine-2,6-dioneYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (74 mg, 0.2 mmol) and benzamidoxime (30 mg, 0.22 mmol) were suspended in dry EtOH (1 ml) and ethanolic sodium ethoxide (21% by wt., 0.111 ml, 0.3 mmol) was added. The mixture was gently warmed until solids were dissolved and then heated in the microwave reactor at 140° C. for 10 min. The mixture was then partitioned between EtOAc and 2M HCl and the organic phase dried (Na2SO4) and evaporated. MDAP afforded the pure title compound (40.7 mg).

Workup

  1. temperatureThe mixture was gently warmed until solids
  2. dissolutionwere dissolved
  3. customThe mixture was then partitioned between EtOAc and 2M HCl
  4. dry with materialthe organic phase dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-27fd95844ea94d7f993b74045578233f
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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