Allyl bromide → HCID 18546874, compound

HRID 1267595Notes

Reaction equation

HRID 1267595 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][NH:8][C:9]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[N:15]=[C:14]3[C:10]=2[NH:11][C:12]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[N:13]3)=[CH:5][CH:4]=1.[CH2:30](Br)[CH:31]=[CH2:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[N:17]=[C:16]([NH:18][CH2:19][CH2:20][CH2:21][OH:22])[N:15]=[C:14]3[C:10]=2[N:11]=[C:12]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[N:13]3[CH:31]([CH3:32])[CH3:30])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18546876HCID 18546876, compound

Product 1

HCID 18546874HCID 18546874, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(4-Methoxybenzylamino)-2,8-bis(3-hydroxypropylamino)purine (0.07 mmol) was stirred in 2 mL dimethylformamide with 0.14 mmol of allylbromide and with 0.36 mmol of dry potassium carbonate at ambient temperature (6 hours). The solvent was evaporated to dryness and the rest extracted between ethylacetate—water. The organic layer was dried, ethylacetate was evaporated and the rest purified by column chromatograpy (silica gel, chloroform). Yield 55%. MS-ESI(+)m/z 441.4 [M+H]+

Workup

  1. customThe solvent was evaporated to dryness
  2. extractionthe rest extracted between ethylacetate—water
  3. customThe organic layer was dried
  4. customethylacetate was evaporated
  5. customthe rest purified by column chromatograpy (silica gel, chloroform)

Sources & evidence

ORD record
ord-55f6de3a66454f9faebfcdfb4bdc1c9d
Source dataset
uspto-grants-2003_04
Patent number
US06552192B1

Reaction notes

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