Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | HCID 86632017 | HCID 86632017 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86632019 | HCID 86632019 | 70.6% |
Reaction Steps
Charge 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yn-2-ol (3.35 g, 1.0 eq), imidazole (2.9 g, 3.0 eq), TEA (2.16 g, 1.5 eq) and diethyl ether (84 mL) at RT. Cool the reaction mass to 0° C. and add trimethyl silyl chloride (1.53 g, 1.0 eq). Stir the reaction mass at RT for 4 h. Monitor the reaction by TLC (5% MeOH in DCM). Charge chilled DM water and extract with diethyl ether. Wash the ether layer with saturated aq. sodium chloride. Dry the organic layer over anhydrous Na2SO4 and concentrate it under vacuum to get the desired compound (3.06 g, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08093383B2 |
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| Source dataset | uspto-grants-2012_01 |
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| ORD ID | ord-f9db649b681947039880319c79a71fce |
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| Source note | uspto-grants-2012_01 |
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