Dimethylformamide → 5-iodo-4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine
Reaction equation
[I:1][C:2]1[C:10]2[C:9]([O:11][CH3:12])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].Cl[Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23]>O>[I:1][C:2]1[C:10]2[C:9]([O:11][CH3:12])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Iodo-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (35, 3.4 g, 12.0 mmol) and 20 mL of N,N-dimethylformamide were combined in a round bottom flask and sodium hydride (350 mg, 8.8 mmol) was added at room temperature. After 20 minutes, chloro-triisopropyl-silane (36, 1.9 mL, 8.8 mmol) was added. The reaction was stirred for 2 hours, then poured into water and extracted 3× with ethyl acetate. The organic layers were combined and washed with brine, then dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel flash column chromatography eluting with 0-25% ethyl acetate in hexane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (37, 1.3 g).
Workup
- extractionextracted 3× with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationthe filtrate concentrated under vacuum
- customThe resulting material was purified by silica gel flash column chromatography
- washeluting with 0-25% ethyl acetate in hexane
- customsolvents removed under vacuum
Sources & evidence
- ORD record
- ord-75ef7f8295f84b04bf4032b214ddf98b
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158636B2
Reaction notes
Loading…