Sodium Thiosulfate → HCID 66584820, compound

HRID 2369010Notes

Reaction equation

HRID 2369010 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][CH:8]([C:10]2[CH:15]=[C:14]([N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:13]3[N:33]=[CH:34][CH:35]=[C:12]3[N:11]=2)[CH3:9])[CH2:3][CH2:2]1.C1C(=O)N([I:43])C(=O)C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[I:43][C:35]1[CH:34]=[N:33][N:13]2[C:14]([N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:22])[CH3:23])=[CH:15][C:10]([CH:8]([NH:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH3:9])=[N:11][C:12]=12

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 66735705HCID 66735705, compound

Product 1

HCID 66584820HCID 66584820, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 5-(1-(tetrahydro-2H-pyran-4-ylamino)ethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.17 g, 0.32 mmol) in acetonitrile (15 ml) at 0° C. was added NIS (78 mg, 0.35 mmol) and stirring continued for 10 minutes. LC/MS showed no starting material (M.W=521) remaining. Saturated sodium thiosulfate solution (˜0.5 ml) was added and stirring continued for 5 minutes. After the acetonitrile was rotoevaporated, the aqueous phase was extracted with DCM (25 ml), washed with water (1×5 ml), brine (1×5 ml), dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with MeOH/EtOAC (0-20%) gave desired product, 3-iodo-5-(1-(tetrahydro-2H-pyran-4-ylamino)ethyl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.14 g, 69%).

Workup

  1. stirringstirring
  2. waitcontinued for 5 minutes
  3. extractionthe aqueous phase was extracted with DCM (25 ml)
  4. washwashed with water (1×5 ml), brine (1×5 ml)
  5. dry with materialdried over MgSO4
  6. customSolvent was removed in vacuo
  7. customthe residue was purified by column chromatography on silica gel
  8. washElution with MeOH/EtOAC (0-20%)

Sources & evidence

ORD record
ord-dbc04f3acf31452d9e5b46a38d32cd85
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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