Methanol → 1-Ethoxycarbonylmethyl-N4-benzoyl cytosine

HRID 535256Notes

Reaction equation

HRID 535256 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:16])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CO>CN(C=O)C.C(Cl)Cl>[CH2:24]([O:23][C:21]([CH2:20][N:13]1[CH:14]=[CH:15][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:11][C:12]1=[O:16])=[O:22])[CH3:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178522337HCID 178522337, compound

Product 1

HCID 120097091-Ethoxycarbonylmethyl-N4-benzoyl cytosineYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 6 (1.92 g, 9 mmol) in dry DMF (100 mL) at 0° C., NaH (0.43 g, 18 mmol) was added and the mixture was stirred at room temperature for 1 h. Ethyl bromoacetate (1.5 g, 9 mmol) was added dropwise at 0° C. and stirred for 1 h. Methanol (2 mL) was added to quench the reaction, and the solvents were removed under reduced pressure. The residue obtained was dissolved in DCM, washed with water (3×50 mL), dried over Na2SO4, and the solvent was evaporated to give 7 as a white solid (1.38 g, 54%).

Workup

  1. stirringstirred for 1 h
  2. customto quench
  3. customthe reaction
  4. customthe solvents were removed under reduced pressure
  5. customThe residue obtained
  6. washwashed with water (3×50 mL)
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d0666185efee491aa6927ea378cc951a
Source dataset
uspto-grants-2014_10
Patent number
US08859490B2

Reaction notes

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