Potassium Carbonate → HCID 57988797, compound

HRID 889003Notes

Reaction equation

HRID 889003 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:7]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[N:6][C:5]=2[N:4]([CH3:25])[C:3]1=[O:26].Br[CH2:28][C:29]#[C:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:37][C:33]1[CH:32]=[C:31]([C:30]#[C:29][CH2:28][N:23]2[CH:24]=[C:20]([C:7]3[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:17])[CH3:18])[C:9]4[C:10](=[O:11])[N:2]([CH3:1])[C:3](=[O:26])[N:4]([CH3:25])[C:5]=4[N:6]=3)[CH:21]=[N:22]2)[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574296571-(3-Bromo-1-propyn-1-yl)-3-fluorobenzeneHCID 57988775HCID 57988775, compound

Product 1

HCID 57988797HCID 57988797, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1,3-dimethyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (obtained following literature procedure U.S. Pat. No. 6,825,349) (0.100 g, 0.27 mmol), 1-(3-Bromo-prop-1-ynyl)-3-fluoro benzene (0.057 g, 0.27 mmol), K2CO3 (0.086 mg, 0.62 mmol) and acetone (5 ml) were refluxed at 80° C. for 5 hrs. The reaction mixture was cooled to room temperature and filtered off solid K2CO3 and evaporated excess of organic solvent under vacuum. The product was purified by column chromatography (2% methanol in dichloromethane) to get pure 8-{1-[3-(3-fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1,3-dimethyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.111 g, 82%).

Workup

  1. customobtained
  2. filtrationfiltered off solid K2CO3
  3. customevaporated excess of organic solvent under vacuum
  4. customThe product was purified by column chromatography (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f965d98c899f4ee68fd0898fc3200471
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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