HCID 57988795, compound → HCID 57429630, compound

HRID 889018Notes

Reaction equation

HRID 889018 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][N:12]2[CH:16]=[C:15]([C:17]3[N:25](COCC[Si](C)(C)C)[C:24]4[C:23](=[O:34])[N:22]([CH2:35][CH2:36][CH3:37])[C:21](=[O:38])[N:20]([CH2:39][CH2:40][CH3:41])[C:19]=4[N:18]=3)[CH:14]=[N:13]2)[CH:6]=[CH:7][CH:8]=1>C(O)C.Cl.C(OCC)(=O)C>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][N:12]2[CH:16]=[C:15]([C:17]3[NH:25][C:24]4[C:23](=[O:34])[N:22]([CH2:35][CH2:36][CH3:37])[C:21](=[O:38])[N:20]([CH2:39][CH2:40][CH3:41])[C:19]=4[N:18]=3)[CH:14]=[N:13]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 57988795HCID 57988795, compound

Product 1

HCID 57429630HCID 57429630, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-{1-[3-(3-hydroxymethyl-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1,3-dipropyl-7-(2-trimethylsilanyl-ethoxymethyl)-3,7-dihydro-purine-2,6-dione (25 mg) in ethanol (3 ml), aq. HCl (2 N, 1 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. The organic layer was washed with water, brine and dried over Na2SO4 and concentrated under vacuum. The residue obtained was purified by column to obtain 8-{1-[3-(3-hydroxymethyl-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (10 mg, 52%) as white solid.

Workup

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

Sources & evidence

ORD record
ord-f694b8a8f326414780544f0811ba18bb
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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