1-Chloromethylnaphthalene → HCID 19356087, compound

HRID 377611Notes

Reaction equation

HRID 377611 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][N:20]1[C:25](=[O:26])[C:24]2=[CH:27][NH:28][N:29]=[C:23]2[N:22]([CH2:30][C:31]([CH3:33])=[CH2:32])[C:21]1=[O:34]>CC(C)=O>[CH3:19][N:20]1[C:25](=[O:26])[C:24]2=[CH:27][N:28]([CH2:2][C:3]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH:6]=[CH:5][CH:4]=3)[N:29]=[C:23]2[N:22]([CH2:30][C:31]([CH3:33])=[CH2:32])[C:21]1=[O:34]

Participants

5

Reactant 3

HCID 68451-ChloromethylnaphthaleneHCID 11430Potassium CarbonateHCID 178448720HCID 178448720, compound

Product 1

HCID 19356087HCID 19356087, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(Chloromethyl)naphthalene (0.214 ml) and potassium carbonate (0.60 g) were added to a suspension of 5-methyl-7-(2-methyl-2-propenyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6[5H,7H]-dione (0.215 g) in acetone (10 ml). The mixture was stirred at room temperature for 16 hours and then heated at reflux for 2 hours. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:hexane (2:1) followed by recrystallisation from ethyl acetate/hexane to give the subtitle compound (0.062 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica eluting with ethyl acetate:hexane (2:1)
  6. customfollowed by recrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9b1d04838254aa7a615cd7b48e66436
Source dataset
uspto-grants-2000_02
Patent number
US06028074

Reaction notes

Loading…