Sodium hydride → HCID 19896193, compound

HRID 1196771Notes

Reaction equation

HRID 1196771 reaction equation
[NH2:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[CH:3][C:4]([O:6]CC)=O.[H-].[Na+].[F:17][C:18]([F:33])([F:32])[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=O)[O:28]CC)=[CH:22][CH:21]=1>CN(C)C=O>[F:17][C:18]([F:32])([F:33])[O:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[NH:1][C:27]2=[O:28])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19896215Ethyl [4-(trifluoromethoxy)phenyl]carbamateHCID 53401888HCID 53401888, compound

Product 1

HCID 19896193HCID 19896193, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.0 g of ethyl 3-amino-3-(2-pyridyl)-2-propenoate was added dropwise to a 20 ml dimethylformamide solution of 0.26 g of sodium hydride (purity: 55%) under stirring at 0° C. This solution was stirred at room temperature for 15 minutes and then added with 1.3 g of ethyl 4-trifluoromethoxyphenylcarbamate. The mixed solution was stirred at 100° C. for 3 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved by adding 100 ml of water and washed with diethyl ether. The obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice. Then precipitated crystals were filtered out and dried under reduced pressure to obtain 1.0 g of 3-(4-trifluoromethoxyphenyl)-6-(2-pyridyl)-2,4(1H,3H)-pyrimidinedione.

Workup

  1. stirringThis solution was stirred at room temperature for 15 minutes
  2. stirringThe mixed solution was stirred at 100° C. for 3 hours
  3. distillationthe solvent was distilled away under reduced pressure
  4. dissolutionThe residue was dissolved
  5. additionby adding 100 ml of water
  6. washwashed with diethyl ether
  7. additionThe obtained aqueous layer was added into a mixed solution of 20 ml of concentrated hydrochloric acid and 50 g of ice
  8. customThen precipitated crystals
  9. filtrationwere filtered out
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-e253501785cf410484f957881a1c014d
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

Loading…