Ethyl Acetate → HCID 57542082, compound

HRID 2353315Notes

Reaction equation

HRID 2353315 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[N:5]2[CH:18]=[CH:19][N:20]=[C:4]2[C:3]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>CCO>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[N:5]2[CH:18]=[CH:19][N:20]=[C:4]2[C:3]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59380350HCID 59380350, compound

Product 1

HCID 57542082HCID 57542082, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl [7-chloro-5-(4-nitrobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (0.383 g, 1.06 mmol) and SnCl2.2H2O (1.44 g, 6.37 mmol) in EtOH (5 mL) was heated at refluxing temperature for 1 hour. After cooling to room temperature, the reaction mixture was poured into sat. NaHCO3 aq. and EtOAc and the resulting white suspension was filtered through a pad of Celite. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give methyl [7-chloro-5-(4-aminobenzyl)imidazo[1,2-c]pyrimidin-8-yl]acetate (0.322 g, 92%).

Workup

  1. temperaturewas heated
  2. temperatureat refluxing temperature for 1 hour
  3. filtrationthe resulting white suspension was filtered through a pad of Celite
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts was washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25b88d8e5f2e43bf9f6dd8dcab4f17e4
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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