2,4-Dioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile → HCID 86723841, compound

HRID 576749Notes

Reaction equation

HRID 576749 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5](C#N)=[CH:4][N:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1.O.N>Br>[F:20][C:17]([F:18])([F:19])[C:13]1[CH:12]=[C:11]([N:3]2[CH:4]=[CH:5][C:6](=[O:8])[NH:7][C:2]2=[O:1])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 27367422,4-Dioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrileHCID 12896473Azane;hydrate

Product 1

HCID 86723841HCID 86723841, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-carbonitrile (prepared in Reference Example 112) (22.7 g) was suspended in hydrobromic acid (48%, 220 ml) and the resulting mixture was stirred with heating under reflux for ten hours. The resulting mixture was cooled to 0° C. and to the reaction solutions was then added 28% ammonia water (145 ml) dropwise, and the precipitated solids were collected by filtration and washed with water to afford 1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (17.8 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for ten hours
  3. filtrationthe precipitated solids were collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-11bb8cdfbbad400b966bd2f804a694c2
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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