Water → HCID 21922761, compound
Reaction equation
[Br:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([N:30](C(OC(C)(C)C)=O)[CH3:31])[N:25]=2)=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:5]([Si](C(C)C)(C(C)C)C(C)C)[CH:6]=1.O1CCCC1.O.C(=O)([O-])O.[Na+]>Cl.O1CCOCC1>[Br:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[N:25]=2)=[C:4]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[NH:5][CH:6]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
472 mg (0.782 mmol) of 4-bromo-3-[2-(N-t-butoxycarbonyl-N-methylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-1-triisopropylsilyl-1H-pyrrole [prepared as described in step (vi) above] were dissolved in 10 of ml tetrahydrofuran, 0.98 ml (3.91 mmol) of a 4N solution of hydrogen chloride in dioxane were added to the solution, and the resulting mixture was stirred for 3 hours at 50° C. At the end of this time, water was added to the reaction mixture and then it was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. This was extracted with ethyl acetate, and the organic extract was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using a 7:3 by volume mixture of hexane and ethyl acetate as the eluant to afford 202 mg (yield 74%) of the title compound as a pale brown amorphous solid.
Workup
- additionwere added to the solution
- extractionThis was extracted with ethyl acetate
- extractionthe organic extract
- concentrationwas concentrated under reduced pressure
- customThe resulting residue was purified by chromatography on a silica gel column
- additionby volume mixture of hexane and ethyl acetate as the eluant
Sources & evidence
- ORD record
- ord-a8c1e00bc8f64bdf9aa5af3c1916556d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122666B2
Reaction notes
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