Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate | HCID 15296367 | — |
| Reactant | HCID 58073044 | HCID 58073044 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58073698 | HCID 58073698 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP7 (method 2) starting from 1.0 g (3.87 mmol) 4-chloro-6-ethyl-5-(6-amino-pyridin-3-ylethynyl)-pyrimidine and 1.18 g (4.6 mmol) 3,9-diazaspiro[5.5]undecane-3-carboxylic acid tert-butyl ester using 1.97 mL (11.6 mmoL) DIPEA in 20 mL acetonitrile. The reaction mixture is stirred at 80° C. over night. 1.6 ml conc. HCl is added the reaction is stirred for 4 hours at 80° C. The solvent is removed under reduced pressure. The residue is taken up to in acetonitrile and K2CO3 is added. The mixture is stirred at 80° C. over night. The solvent is removed and the residue is taken up in DCM/water. After phase separation the organic phase is extracted twice with DCM. The combined organic layers are dried over Na2SO4, filtered and the solvent is removed under reduced pressure yielding 1.08 g (74%) of crude product, which is used without further purification in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618111B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-c4e37040d55745889ef2a0bc17bcd8d9 |
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| Source note | uspto-grants-2013_12 |
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