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

HRID 1097668Notes

Reaction equation

HRID 1097668 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]=[C:36]([F:38])[CH:35]=[CH:34][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[CH:34]=[CH:35][C:36]([F:38])=[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 66812467Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoateHCID 178506463HCID 178506463, compound

Product 1

HCID 593954008-Chloro-1-(3-{3-[(2-chloro-4-fluorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneYield 67.2%

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-chloro-4-fluorophenyl)-N-hydroxyethanimidamide (42 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. The crude product was purified on the MDAP. The product fractions were combined and concentrated to give the title compound as a white solid (65 mg, 67%).

Workup

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

Sources & evidence

ORD record
ord-17f1a5cc83364361a3aef81a447b2353
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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