Dimethylformamide → HCID 57988783, compound

HRID 889029Notes

Reaction equation

HRID 889029 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].[CH:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44](=[O:45])[CH2:43][CH:42]([CH2:46]OS(C)(=O)=O)[CH2:41]2)=[CH:36][CH:35]=1)([CH3:33])[CH3:32].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44](=[O:45])[CH2:43][CH:42]([CH2:46][N:25]3[CH:26]=[C:22]([C:9]4[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:21])[CH3:19])[C:11]5[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]=5[N:8]=4)[CH:23]=[N:24]3)[CH2:41]2)=[CH:36][CH:35]=1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10018358HCID 10018358, compoundHCID 116261941,3-dipropyl-8-(1H-pyrazol-4-yl)-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 57988783HCID 57988783, compoundYield 80.5%

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 1-(4-isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl ester (0.107 g, 0.34 mmol), K2CO3 (0.048 g, 0.34 mmol) and DMF (1 ml) were heated at 75-80° C. for 16 hrs. Reaction mixture was cooled to 20-25° C. and water was added (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-[1-(4-isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (0.12 g, 80%) as a light yellow oil.

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-c12842fb483c4cecae1b3b7d31d2c054
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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