Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | 1,3-Dibromo-5,5-dimethylhydantoin | HCID 6479 | — |
| Reactant | HCID 59232069 | HCID 59232069 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59232026 | HCID 59232026 | 184.1% |
Reaction Steps
To a solution of 2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanol (777 mg, 4.3 mmol) in DMF (22 mL) at −20° C. (IPA and dry ice) was added 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione (359 mg, 1.72 mmol) ) was added in 4 portions within 20 min. The reaction was stirred at −20° C. for 30 min. Analytical HPLC indicated 22% starting material remanded, additional B (90 mg, 0.30 mmol) was added and stirred for 20 min. The reaction was quenched with satd. Na2SO3 and warmed up to rt. The crude was extracted w/EtOAc 5×. The organic was washed with 5% aq K2CO3 and brine. Dried over Na2SO4 and concentrated. The crude was purified by MPLC with 0-7% MeOH/CH2Cl2 to give 814 mg of desired product (yield, 72.6%). MS [M+H]+=257.3; LCMS RT=1.14 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08143393B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-25076a287c4742a6ba7bf06ad10af923 |
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| Source note | uspto-grants-2012_03 |
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