Potassium Carbonate → HCID 178525929, compound

HRID 1779878Notes

Reaction equation

HRID 1779878 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[N:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]C)=[O:28]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]([CH2:26][C:27]([OH:29])=[O:28])[C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[N:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178522340HCID 178522340, compound

Product 1

HCID 178525929HCID 178525929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-benzyloxycarbonyl cytosine (0.317 mol) and potassium carbonate (0.317 mol) in dimethylformamide (900 ml) is added methyl bromoacetate (0.317 mol) and the mixture is stirred vigorously overnight under nitrogen. The mixture is filtered, washed with ether and evaporated to dryness, in vacuo. The solid residue is treated with water (300 ml) and 4N hydrochloric acid (12 ml), stirred for 20 minutes at 0° C., filtered and washed with water (2×100 ml). The precipitate is treated with water and 2N sodium hydroxide (60 ml), and is boiled for 10 minutes. The mixture is cooled to 0° C., filtered, and precipitated by the addition of 4N hydrochloric acid (70 ml) to afford the pure title compound.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with ether
  3. customevaporated to dryness, in vacuo
  4. additionThe solid residue is treated with water (300 ml) and 4N hydrochloric acid (12 ml)
  5. stirringstirred for 20 minutes at 0° C.
  6. filtrationfiltered
  7. washwashed with water (2×100 ml)
  8. additionThe precipitate is treated with water and 2N sodium hydroxide (60 ml)
  9. waitis boiled for 10 minutes
  10. filtrationfiltered
  11. customprecipitated by the addition of 4N hydrochloric acid (70 ml)

Sources & evidence

ORD record
ord-0e812c50bad040999f339dc8a15b3304
Source dataset
uspto-grants-1997_05
Patent number
US05629152

Reaction notes

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