HCID 57988766, compound → HCID 57429648, compound

HRID 889050Notes

Reaction equation

HRID 889050 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[C:16]([C:18]4[N:26](COCC[Si](C)(C)C)[C:25]5[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22](=[O:39])[N:21]([CH2:40][CH2:41][CH3:42])[C:20]=5[N:19]=4)[CH:15]=[N:14]3)[CH2:8]2)=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[CH:17]=[C:16]([C:18]4[NH:26][C:25]5[C:24](=[O:35])[N:23]([CH2:36][CH2:37][CH3:38])[C:22](=[O:39])[N:21]([CH2:40][CH2:41][CH3:42])[C:20]=5[N:19]=4)[CH:15]=[N:14]3)[CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 57988766HCID 57988766, compound

Product 1

HCID 57429648HCID 57429648, compoundYield 158%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-{1-[5-(4-Fluoro-benzyl)-4,5-dihydro-isoxazol-3-ylmethyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (80 mg) in ethanol (5 ml) aq. HCl (2 N, 5 ml) was added and the reaction mixture was refluxed for 2 hrs. The volatiles were evaporated and the residue obtained was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue obtained was purified by column chromatography to obtain 8-{1-[5-(4-Fluoro-benzyl)-4,5-dihydro-isoxazol-3-ylmethyl]-1H-pyrazol-4-yl}-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (100 mg, 98%) as white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hrs
  2. customThe volatiles were evaporated
  3. customthe residue obtained
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-db5de5b9539b453d8c5301b42f3fd595
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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