HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 178433070, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-bromo-4-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine | HCID 59258848 | — |
| Reactant | HCID 178479277 | HCID 178479277 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 178433070 | HCID 178433070 | 88% |
Reaction Conditions
| Temperature | 160 °C |
|---|
Reaction Steps
A mixture of 5-bromo-4-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine (5.00 g, 17.0 mmol), cis-4-aminocyclohexanol hydrochloride (2.77 g, 18.3 mmol), and diisopropylethyl amine (8.69 mL, 49.9 mmol) in dimethylacetamide (60.0 mL) was heated at 160° C. in a sealed tube overnight. The reaction mixture was concentrated and the residue was purified by flash chromatography eluting with chloroform/methanol (0-3%). Combined fractions containing the desired product were concentrated. The resulting gum was dissolved in methyl tert-butyl ether (450 mL) and the solution was washed with 50% brine, dried (MgSO4), filtered and concentrated to afford the title compound as a orange foamy solid (5.53 g, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08273755B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-b84cae98b81c493d8ffa8a3481a91e70 |
| Source note | uspto-grants-2012_09 |