Cesium carbonate → 8-(1-{2-oxo-2-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione

HRID 889047Notes

Reaction equation

HRID 889047 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[N:8][C:7]=2[N:6]([CH2:27][CH2:28][CH3:29])[C:5]1=[O:30])[CH2:2][CH3:3].Br[CH2:32][C:33]([CH:35]1[CH2:39][N:38]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=2)[C:37](=[O:50])[CH2:36]1)=[O:34].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[O:34]=[C:33]([CH:35]1[CH2:36][C:37](=[O:50])[N:38]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:47])[F:48])[CH:41]=2)[CH2:39]1)[CH2:32][N:25]1[CH:26]=[C:22]([C:9]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[C:11]3[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:30])[N:6]([CH2:27][CH2:28][CH3:29])[C:7]=3[N:8]=2)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 116261941,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dioneHCID 57429668HCID 57429668, compound

Product 1

HCID 579887718-(1-{2-oxo-2-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dioneYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.200 g, 0.462 mmol), 4-(2-Bromo-acetyl)-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (0.240 g, 0.693 mmol), Cs2CO3 (0.30 g, 0.924 mmol) and acetonitrile (2 ml) were heated at 90-100° C. in a sealed tube for 6 hrs. Reaction mixture was cooled to 20-25° C. and filtered off. The organic volatiles were evaporated. The crude product was purified by preparative TLC to obtain pure 8-(1-{2-oxo-2-[5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-ethyl}-1H-pyrazol-4-yl)-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.090 g, 28%) as a brown mass.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. filtrationfiltered off
  4. customThe organic volatiles were evaporated
  5. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-7692494d795e4fe5a595703838ae9000
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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