Water → HCID 50941864, compound

HRID 1396710Notes

Reaction equation

HRID 1396710 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]2[S:8][C:9]3[N:10]=[C:11]([NH2:18])[N:12]=[C:13]([S:16][CH3:17])[C:14]=3[N:15]=2)=[CH:4][CH:3]=1.[OH-].[Na+].I[CH3:24].O>CS(C)=O>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([C:7]2[S:8][C:9]3[N:10]=[C:11]([NH2:18])[N:12]=[C:13]([S:16][CH3:17])[C:14]=3[N:15]=2)[CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 50941767HCID 50941767, compound

Product 1

HCID 50941864HCID 50941864, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(4-fluorobenzyl)-7-(methylthio)thiazolo[5,4-d]pyrimidin-5-amine (0.4 g, 1.31 mmol) and 2N NaOH (0.65 ml, 1.31 mmol) in DMSO (7 ml) was added iodomethane (81 μl, 1.31 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into water and extracted with ethyl acetate, brine and dried over Na2SO4. After removing the solvents under reduced pressure, the residue was purified by chromatography on silica gel (hexane/EtOAc 5:1) yielding the title compound as a white solid (0.29 g, 69%).

Workup

  1. extractionextracted with ethyl acetate, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removing the solvents under reduced pressure
  4. customthe residue was purified by chromatography on silica gel (hexane/EtOAc 5:1)

Sources & evidence

ORD record
ord-0372b5553a9744d988d8de4fa5090b9a
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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