Sodium ethoxide → HCID 59395885, compound

HRID 1097655Notes

Reaction equation

HRID 1097655 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=O)[C:6](=[O:20])[N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[N:3]=1.O[NH:27][C:28](=[NH:35])[CH2:29][C:30]1[CH:34]=[CH:33][S:32][CH:31]=1.CC[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][C:15]3[O:17][N:35]=[C:28]([CH2:29][C:30]4[CH:34]=[CH:33][S:32][CH:31]=4)[N:27]=3)[C:6](=[O:20])[N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 59395791HCID 59395791, compoundHCID 178510853HCID 178510853, compound

Product 1

HCID 59395885HCID 59395885, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 4-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (70 mg, 0.19 mmol), N-hydroxy-2-(3-thienyl)ethanimidamide (36 mg, 0.23 mmol), 21% solution of NaOEt in EtOH (78 μl, 0.21 mmol) and 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 and the aqueous layer extracted again with EtOAc. The combined extracts were concentrated and purified by MDAP. The title compound was freeze dried from 1,4-dioxane to give a white solid (27 mg, 31%).

Workup

  1. temperatureAfter cooling the reaction
  2. customwas partitioned between 2M HCl (aq) and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted again with EtOAc
  5. concentrationThe combined extracts were concentrated
  6. custompurified by MDAP
  7. dry with materialdried from 1,4-dioxane

Sources & evidence

ORD record
ord-d4380c3a96754c778c59d111c11b0cf4
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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