Isopropanol → HCID 86726464, compound
Reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].[Cl:7][C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1>C1COCC1>[Cl:7][C:8]1[N:9]=[C:10]([O:6][CH:4]([CH3:5])[CH3:3])[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1Participants
Procedure
To a suspension of sodium hydride (1 equiv, 60% in mineral oil) in dry THF (0.9 M) under nitrogen atmosphere was added propan-2-ol (0.52 equiv). The reaction mixture was stirred at room temperature for 30 min before a solution of 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (0.5 equiv) in dry THF (0.45 M) was added. The mixture was stirred at room temperature for 1 h. The reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether) to afford the title compound as a yellow oil (81% yield). MS (ESI) m/z 468.2 [M+1]+.
Workup
- additionwas added
- customUpon completion, the reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-ef922f1edf504f1d90ce9afbedb5e03d
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346812B2
Reaction notes
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