Potassium Carbonate → Methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionate

HRID 1862237Notes

Reaction equation

HRID 1862237 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[SH:22].C(=O)([O-])[O-].[K+].[K+].Cl[C:30]1[N:35]=[C:34]([O:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[CH3:38])[CH:33]=[CH:32][N:31]=1>C(#N)C>[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:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[S:22][C:30]1[N:35]=[C:34]([O:36][CH:37]([CH3:38])[C:39]([O:41][CH3:42])=[O:40])[CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120567412-Chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidineHCID 186192703-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 18619236Methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.40 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenyl mercaptan was dissolved in 6 ml of acetonitrile, to this solution was added 0.31 g of potassium carbonate, and the mixture was stirred for 30 minutes, then, 0.29 g of 2-chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidine was added and the mixture was stirred for 3 hours. This reaction solution was poured into ice water, 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 0.46 g of methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionate [present compound 6-2].

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6550ebd7c2434a1bbb05773d82a8606e
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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