Potassium Carbonate → 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 925552Notes

Reaction equation

HRID 925552 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[NH:21][C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][Si:38]([CH3:45])([CH3:44])[CH2:39][CH2:40][O:41][CH2:42]Cl>CN(C=O)C.O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[N:21]([CH2:42][O:41][CH2:40][CH2:39][Si:38]([CH3:45])([CH3:44])[CH3:37])[C:20]3[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17]([N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)=[N:16][C:15]=3[N:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 671350988-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-1,7-dihydro-purin-6-one

Product 1

HCID 671351238-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-oneYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 8-(1-Benzyl-1H-pyrazol-4-yl)-1-propyl-2-pyrrolidin-1-yl-1,7-dihydro-purin-6-one (0.83 g, 2.1 mmol) and potassium carbonate (0.857 g, 6.2 mmol) was taken in DMF (5 ml) and 2-(trimethylsilyl)ethoxymethyl chloride (1.0 ml, 6.2 mmol) was added drop wise at 0° C. and the mixture was stirred at 20° C. for 4 hours. The mixture was cooled to 10° C. and diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate (3×15 ml). The organic layer was washed with saturated brine solution (2×15 ml) and dried over Na2SO4. Solvent was evaporated and the residue was further purified by column chromatography to obtain the above product as pale yellow semisolid (0.325 g, 30%)

Workup

  1. temperatureThe mixture was cooled to 10° C.
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×15 ml)
  3. washThe organic layer was washed with saturated brine solution (2×15 ml)
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customthe residue was further purified by column chromatography

Sources & evidence

ORD record
ord-1a800b99cde246b4b75c02ccb45b2bcc
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

Loading…