Sodium ethoxide → HCID 59395404, compound

HRID 1097704Notes

Reaction equation

HRID 1097704 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:16]([O:18]C)=O)[C:6](=[O:20])[N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[N:3]=1.[CH3:26][CH2:27][O-].[Na+]>CCO>[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:16]3[O:18][N:10]=[C:2]([C:26]4[CH:27]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:3]=3)[C:6](=[O:20])[N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 59405258HCID 59405258, compound

Product 1

HCID 59395404HCID 59395404, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of methyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (50 mg, 0.13 mmol), benzamidine oxime (20 mg, 0.15 mmol) and a 21% solution of NaOEt in EtOH (76 μl, 0.20 mmol) in EtOH (1.5 ml) was heated in the microwave at 140° C. for 10 min. After cooling the reaction was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, dried (MgSO4) and concentrated. Purification by the MDAP gave the title compound as a white solid (25 mg, 41%).

Workup

  1. temperatureAfter cooling the reaction
  2. customwas partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by the MDAP

Sources & evidence

ORD record
ord-d364f11887104380a25217916987a292
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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