Trityl chloride → HCID 68253447, compound

HRID 2405892Notes

Reaction equation

HRID 2405892 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[NH:10][N:11]=[C:12]([I:13])[C:5]=12)[CH3:2].[H-].[Na+].[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:1]([O:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:11]=[C:12]([I:13])[C:5]=12)[CH3:2]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178467449HCID 178467449, compound

Product 1

HCID 68253447HCID 68253447, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of iodo mixture-4-ethoxy-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (1.40 g, 4.823 mmol) in DMF (20 mL) cooled to 0° C., was added NaH (212.2 mg, 5.31 mmol, 60% dispersion in oil). The reaction mixture was stirred at this temperature for 30 minutes and then trityl chloride (1.41 g, 5.06 mmol) was added in one portion. The reaction mixture was allowed to warm to ambient temperature over 18 hours. After this time, the reaction mixture was concentrated in vacuo, diluted with DCM and water. The organic layer was separated and washed with saturated aqueous brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (ISCO Companion™, 120 g column, eluting with DCM) to give the sub title compound as a mixture of regioisomers (592 mg, 23% Yield). 1H NMR (400 MHz, DMSO) δ 8.27 (1H, s), 7.34-7.12 (15H, m), 4.55 (3H, q) and 1.40 (2H, t).

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM and water
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by column chromatography (ISCO Companion™, 120 g column, eluting with DCM)

Sources & evidence

ORD record
ord-d887787330004845a4871d95b836f4c9
Source dataset
uspto-grants-2014_08
Patent number
US08809335B2

Reaction notes

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