HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Bicarbonate → (S)-2-benzyl 3-ethyl 8-(2-amino-6-((4-bromophenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Benzyl 3-ethyl (3S)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate | HCID 117941765 | — |
| Reactant | 4-((4-Bromophenoxy)methyl)-6-chloropyrimidin-2-amine | HCID 117942029 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (S)-2-benzyl 3-ethyl 8-(2-amino-6-((4-bromophenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate | HCID 117952362 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 4-((4-Bromophenoxy)methyl)-6-chloropyrimidin-2-amine (454 mg, 1.4 mmol), (S)-2-benzyl 3-ethyl 2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (500 mg, 1.44 mmol) and NaHCO3 (605 mg, 7 mmol) in dioxane (5 mL) was heated to 100° C. for 12 h. The reaction was cooled to RT, concentrated in vacuo, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification on normal phase silica gel (EtOAc/petroleum ether) provided (S)-2-benzyl 3-ethyl 8-(2-amino-6-((4-bromophenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199994B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b29fc1474d934fceb9e18789e9773a41 |
| Source note | uspto-grants-2015_12 |