Dimethylformamide → HCID 57988799, compound

HRID 889035Notes

Reaction equation

HRID 889035 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].[O:31]=[C:32]1[CH:36]([CH2:37]OS(C)(=O)=O)[CH2:35][CH2:34][N:33]1[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:52])([F:51])[F:50])[CH:44]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[O:31]=[C:32]1[CH:36]([CH2:37][N:25]2[CH:26]=[C:22]([C:9]3[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[C:11]4[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]=4[N:8]=3)[CH:23]=[N:24]2)[CH2:35][CH2:34][N:33]1[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:51])([F:50])[F:52])[CH:44]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 116261941,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dioneHCID 57988792HCID 57988792, compound

Product 1

HCID 57988799HCID 57988799, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77.5 °C

Procedure

A mixture of 1,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.100 g, 0.23 mmol), methanesulfonic acid 2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl ester (0.10 g, 0.32 mmol), K2CO3 (0.045 g, 0.32 mmol) and DMF (1 ml) was heated at 75-80° C. for 16 hrs. Reaction mixture was cooled to 20-25° C. and diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate, washed with saturated brine solution. The organic layer was dried over Na2SO4 and evaporated to obtain crude product (0.2 g). The crude product was purified by preparative TLC to obtain pure 8-{1-[2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.10 g, 65%).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with saturated brine solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated
  7. customto obtain crude product (0.2 g)
  8. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-f9fc8a529e4f47b488e766b185ec0085
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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