Triethylamine → HCID 57429631, compound

HRID 889019Notes

Reaction equation

HRID 889019 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]#[CH:21])[CH:18]=3)=[N:8][C:7]=2[N:6]([CH2:22][CH2:23][CH3:24])[C:5]1=[O:25])[CH2:2][CH3:3].I[C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[O:25]=[C:5]1[N:6]([CH2:22][CH2:23][CH3:24])[C:7]2[N:8]=[C:9]([C:14]3[CH:15]=[N:16][N:17]([CH2:19][C:20]#[C:21][C:27]4[CH:32]=[CH:31][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:28]=4)[CH:18]=3)[NH:10][C:11]=2[C:12](=[O:13])[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 132184-IodobenzenesulfonamideHCID 57988794HCID 57988794, compound

Product 1

HCID 57429631HCID 57429631, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3-dipropyl-8-(1-prop-2-ynyl-1H-pyrazol-4-yl)-3,7-dihydro-purine-2,6-dione (200 mg, 0.59 mmol), 4-iodo-benzenesulfonamide (166 mg, 0.59 mmol), copper iodide (10 mg, 0.059 mmol), dichlorobis (triphenylphosphine)-palladium (II) (21 mg, 0.03 mmol), triethylamine (2 ml), DMF (2 ml) was degassed for 10 min. and stirred for 20 hrs at room temperature. The reaction mixture was diluted with water (10 ml) and extracted with DCM (3×10 ml). Organic layer was washed with brine (2×15 ml) and dried over Na2SO4. The organic volatile solvent was evaporated and the crude product was purified using HPLC to obtain pure 4-{3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-pyrazol-1-yl]-prop-1-ynyl}-benzenesulfonamide (4.2 mg, 2%).

Workup

  1. customwas degassed for 10 min.
  2. additionThe reaction mixture was diluted with water (10 ml)
  3. extractionextracted with DCM (3×10 ml)
  4. washOrganic layer was washed with brine (2×15 ml)
  5. dry with materialdried over Na2SO4
  6. customThe organic volatile solvent was evaporated
  7. customthe crude product was purified

Sources & evidence

ORD record
ord-e5796740f663414e8c64bf6f85fca2a9
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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