Hydrochloric Acid → HCID 18619233, compound

HRID 1862232Notes

Reaction equation

HRID 1862232 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][C:5]1[C:6]([OH:11])=[N:7][NH:8][C:9]=1[CH3:10].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:35][O:34][C:32]([CH2:31][O:11][C:6]1[C:5]([O:4][C:3]2[CH:12]=[C:13]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[C:14]([F:16])=[CH:15][C:2]=2[Cl:1])=[C:9]([CH3:10])[NH:8][N:7]=1)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178433724HCID 178433724, compound

Product 1

HCID 18619233HCID 18619233, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.21 g of 4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-3-hydroxy-5-methylpyrazole in 1.0 ml of N,N-dimethylformamide were added 0.10 g of methyl bromoacetate and 0.20 g of potassium carbonate, and the mixture was stirred for 3 hours at room temperature. Dilute hydrochloric acid was poured into this reaction solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate. This solution was subjected to silica gel column chromatography to obtain 0.06 g of 3-(methoxycarbonyl)methoxy-4-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-5-methylpyrazole [present compound 5-17].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-9a5d81bd356c4ee79a6ee25934fa9f4b
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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