HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Ethyl 3-amino-4,4,4-trifluorocrotonate | HCID 5702529 | — |
| Reactant | ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate | HCID 18315064 | — |
| Reactant | Sodium trimethylsilanolate | HCID 23672319 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione | HCID 18315080 | — |
Reaction Steps
This compound was prepared using 4.0 grams (0.036 mole) of sodium trimethylsilanolate, 6.6 grams (0.036 mole) of ethyl 3-amino4,4,4-trifluorocrotonate, 8.5 grams (0.032 mole) of ethyl N-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)carbamate, and 2.2 grams (0.014 mole) of DBU in 75 mL of DMF. This preparation differs from well-known literature preparations for pyrimidinedione rings in that sodium trimethylsilanolate and DBU were used rather than sodium hydride. The yield of title compound was 1.7 grams. The NMR spectrum was consistent with the proposed structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06352958B1 |
| Source dataset | uspto-grants-2002_03 |
| ORD ID | ord-b0d1e0b5359340c1aa863386b79bc1a2 |
| Source note | uspto-grants-2002_03 |