Sodium ethoxide → HCID 90402617, compound

HRID 2200625Notes

Reaction equation

HRID 2200625 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([NH:13][C:14](=[O:34])[NH:15][C:16]2[N:17]=[CH:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:20]=2[C:21]([O:23]CC)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+]>C(O)C>[CH2:1]([O:8][CH:9]1[CH2:10][CH:11]([N:13]2[C:21](=[O:23])[C:20]3[N:19]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[CH:18]=[N:17][C:16]=3[NH:15][C:14]2=[O:34])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 90402937HCID 90402937, compound

Product 1

HCID 90402617HCID 90402617, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(3-(3-(benzyloxy)cyclobutyl)ureido)-1-(4-chlorobenzyl)-1H-imidazole-5-carboxylate (310 mg, 0.64 mmol) in ethanol (50 mL) was added freshly prepared sodium ethoxide (87.4 mg, 1.28 mmol) and the reaction was heated at reflux for 4 h. The reaction was cooled and concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was dried and concentrated to give 1-(3-(benzyloxy)cyclobutyl)-7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dione (240 mg, 85.5% yield) as a yellow solid. LCMS retention time 1.764 min; LCMS MH+ 437.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between ethyl acetate and brine
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e152f558c78449cdaf75576d8e2be4f4
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…