1-Bromo-3-chloropropane → 1-(3-chloropropyl)-N4-acetylcytosine

HRID 1896068Notes

Reaction equation

HRID 1896068 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[N:6]=1)(=[O:3])[CH3:2].Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][CH2:15][CH2:14][CH2:13][N:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:6][C:7]1=[O:11]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178474340HCID 178474340, compound

Product 1

HCID 581660611-(3-chloropropyl)-N4-acetylcytosine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-acetylcytosine, 1-bromo-3-chloropropane, and potassium carbonate in DMF was stirred at room temperature under argon for 4 days, filtered and evaporated to dryness. The crude product was purified by column chromatography and gave 1-(3-chloropropyl)-N4-acetylcytosine.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8092625e25f04ed7bbd0dd95aefc6395
Source dataset
uspto-grants-2013_08
Patent number
US08518885B2

Reaction notes

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