HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-n-Butyl-1-(2'-carboxybiphen-4-yl)methyl-5,6-dimethylpyrimidin-4(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate | HCID 9906257 | — |
| Reactant | 4-Amino-2-n-butyl-5,6-dimethylpyrimidine | HCID 19902235 | — |
| Reactant | HCID 21791174 | HCID 21791174 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-n-Butyl-1-(2'-carboxybiphen-4-yl)methyl-5,6-dimethylpyrimidin-4(3H)-one | HCID 131717222 | — |
Reaction Steps
Heating 4-amino-2-n-butyl-5,6-dimethylpyrimidine (from Example 23) with 4-bromomethyl-2'-t-butoxycarbonylbiphenyl in an appropriate solvent such as methanol or DMF, followed by treatment of the intermediate pyrimidinium species with aqueous base such as 0.1N sodium hydroxide as described by Brown, Hoerger, and Mason (J. Chem. Soc., 1955, 4035), followed by treatment with neat trifluoroacetic acid to achieve final deprotection for the carboxyl group, would provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05100897 |
| Source dataset | uspto-grants-1992_03 |
| ORD ID | ord-a354a3fc9ede4077ab7a1788ba6a846b |
| Source note | uspto-grants-1992_03 |