N-Iodosuccinimide → 5-Iodo-7H-pyrrolo[2,3-d]pyrimidine
Reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[I:10]N1C(=O)CCC1=O>C(#N)C>[I:10][C:9]1[C:5]2[CH:4]=[N:3][CH:2]=[N:1][C:6]=2[NH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 7H-pyrrolo[2,3-d]pyrimidine (Preparation 202, 28.0 g, 235 mmol) and N-iodosuccinimide (55.4 g, 246 mmol) in acetonitrile (470 mL) was stirred at room temperature for 16 hours. The solids were filtered, rinsed with acetonitrile (150 mL) and dried in vacuo. The solid was dissolved in 1.5 L of 1N aqueous sodium hydroxide solution and to it was added 2N aqueous hydrogen chloride solution until ˜pH 9. The resulting precipitate was filtered, rinsed with water (300 mL), and dried in vacuo for 16 hours at 70° C., ˜10 mbar, to afford the title compound in 81% yield, 46.84 g.
Workup
- filtrationThe solids were filtered
- washrinsed with acetonitrile (150 mL)
- customdried in vacuo
- dissolutionThe solid was dissolved in 1.5 L of 1N aqueous sodium hydroxide solution and to it
- additionwas added 2N aqueous hydrogen chloride solution until ˜pH 9
- filtrationThe resulting precipitate was filtered
- washrinsed with water (300 mL)
- customdried in vacuo for 16 hours at 70° C.
Sources & evidence
- ORD record
- ord-f409a75c58cd44738a7c6792df30c2bb
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846698B2
Reaction notes
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