4-Toluenesulfonyl chloride → 2,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine
Reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CN(C1C=CC=CN=1)C>C(Cl)Cl.C(OC(=O)C)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[C:6]=2[N:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 2,4-dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.58 g, 2.86 mmol) in CH2Cl2 (6 mL) was added diisopropylethylamine (DIPEA) (0.56 mL, 3.14 mmol) and p-toluenesulfonyl chloride (TsCl) (0.57 g, 3.0 mmol), followed by dimethylaminopyridine (DMAP) (0.035 g, 0.286 mmol). After stirring at ambient temperature for 1 h, the solution was diluted with ethylacetate, and the organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine. The organic extract was then dried over Na2SO4 and concentrated to give a crude residue, which was purified by flash column (hexanes/ethyl acetate, 5:1) to yield 2,4-dichloro-5-methyl-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.38 g, 38%).
Workup
- washthe organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine
- extractionThe organic extract
- dry with materialwas then dried over Na2SO4
- concentrationconcentrated
- customto give a crude residue, which
- customwas purified by flash column (hexanes/ethyl acetate, 5:1)
Sources & evidence
- ORD record
- ord-356ec8cd4d0241ee91dabdd5ca5ab811
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705004B2
Reaction notes
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