N-Iodosuccinimide → 2-Butyl-4-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine
Reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:13]1[N:14]=[C:15]([Cl:22])[C:16]2[NH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)[CH2:10][CH2:11][CH3:12]>C1COCC1.CC(OC)(C)C>[CH2:9]([C:13]1[N:14]=[C:15]([Cl:22])[C:16]2[NH:21][CH:20]=[C:19]([I:1])[C:17]=2[N:18]=1)[CH2:10][CH2:11][CH3:12]Participants
Procedure
N-Iodosuccinimide (2.09 g, 9.29 mmol) was added portionwise to a stirred solution of 2-butyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.69 g, 8.06 mmol) in THF (35 mL). The resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with TBME (50 mL) then washed with aqueous sodium thiosulphate solution (50 mL) then saturated aqueous sodium chloride solution (20 mL). The organic phase was dried (Na2SO4), filtered and evaporated. The sample was dissolved in dichloromethane and purified by chromatography on silica using a gradient of 0-100% dichloromethane-cyclohexane over 30 minutes followed by a gradient of 0-100% TBME-cyclohexane followed by 0-20% methanol over 15 minutes. The appropriate fractions were identified by LC-MS then combined and evaporated in vacuo to give the title compound as a yellow solid (2.2 g).
Workup
- washthen washed with aqueous sodium thiosulphate solution (50 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- dissolutionThe sample was dissolved in dichloromethane
- custompurified by chromatography on silica using a gradient of 0-100% dichloromethane-cyclohexane over 30 minutes
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-42c0e598aeba4a2cae89c79fd0efaa12
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428512B2
Reaction notes
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