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

HRID 1097667Notes

Reaction equation

HRID 1097667 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15]C(OCC)=O)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1.CC[O-].[Na+].[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=1[CH2:39]/[C:40](=[N:43]/[H])/[NH:41][OH:42]>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[O:42][N:41]=[C:40]([CH2:39][C:33]4[C:34]([Cl:38])=[CH:35][CH:36]=[CH:37][C:32]=4[Cl:31])[N:43]=3)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27581642-(2,6-Dichloro-phenyl)-N-hydroxy-acetamidineHCID 66812467Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate

Product 1

HCID 593956358-Chloro-1-(3-{3-[(2,6-dichlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
140 °C

Procedure

Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (70 mg, 0.19 mmol) was dissolved in EtOH. The solution was treated with a 21% solution of NaOEt in EtOH (78 μl, 0.21 mmol) and (1Z)-2-(2,6-dichlorophenyl)-N-hydroxyethanimidamide (46 mg, 0.21 mmol). The reaction was heated in the microwave at 140° C. for 10 min. The mixture was partitioned between EtOH and 2M HCl (aq). The organic layer was decanted off and concentrated by nitrogen blowdown. The crude product was purified on the MDAP. The product fractions were combined and concentrated to give the title compound as a white solid (80 mg, 80%).

Workup

  1. customThe mixture was partitioned between EtOH and 2M HCl (aq)
  2. customThe organic layer was decanted off
  3. concentrationconcentrated by nitrogen
  4. customThe crude product was purified on the MDAP
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a97353d37e9a4e8a86a479c19ba01fe0
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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