Sodium hydride → 4-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1821594Notes

Reaction equation

HRID 1821594 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:3]=12.[CH3:20][Si:21]([CH3:29])([CH3:28])[CH2:22][CH2:23][O:24][CH:25](Cl)Cl.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[N:10]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:29])([CH3:28])[CH3:20])[N:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866110432-(Trimethylsilyl)-ethoxymethylene chlorideHCID 178503465HCID 178503465, compound

Product 1

HCID 578933704-Chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidineYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (2.30 g, 7.39 mmol) and 2-(trimethylsilyl)-ethoxymethylene chloride (1.96 mL, 11.086 mmol) in dry DMF (40 mL) at 0° C. under nitrogen was added sodium hydride (0.354 g of 60% solids in mineral oil, 14.78 mmol). The reaction mixture was stirred for two hours and allowed to warm to room temperature during this time. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was separate, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (01% to 20% EtOAc in hexanes) to give 2.30 g of 4-chloro-3-(2-chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidine

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe organic layer was separate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica (01% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d25ffac6c47043adb33dc2078e34288f
Source dataset
uspto-grants-2009_10
Patent number
US07608603B2

Reaction notes

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