Hydrochloric Acid → HCID 18619261, compound

HRID 1862235Notes

Reaction equation

HRID 1862235 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[OH:22].C(N(CC)CC)C.Cl[CH:31]([C:36]([CH3:38])=[O:37])[C:32]([O:34][CH3:35])=[O:33].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[O:22][CH:31]([C:36](=[O:37])[CH3:38])[C:32]([O:34][CH3:35])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 107332Methyl 2-chloroacetoacetate2×HCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 18619261HCID 18619261, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol was dissolved in 30 ml of N,N-dimethylformamide, to this was added 5.0 ml of triethylamine, then 5.0 g of methyl 2-chloroacetoacetate was added to the resulted mixture at room temperature with stirring. Then, stirring was continued for 10 minutes at room temperature and for 1 hour at 60° C. 2.0 ml of triethylamine and 2.0 g of methyl 2-chloroacetoacetate were added to this solution, then, the mixture was further stirred for 1 hour at 60° C. The reaction solution was stirred overnight at room temperature, then, the reaction solution was poured into ice water and dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 7.86 g methyl 2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-oxobutyrate.

Workup

  1. stirringThen, stirring
  2. stirringthe mixture was further stirred for 1 hour at 60° C
  3. stirringThe reaction solution was stirred overnight at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-981b745b5ff54481986062347f9148f6
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

Loading…