Methanol → Methyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate

HRID 432559Notes

Reaction equation

HRID 432559 reaction equation
CO.[Cl:3][C:4]1[CH:25]=[C:24]([F:26])[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])=[CH:22][C:5]=1[O:6][CH2:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[O:10][CH:11]([CH3:17])[C:12]([O:14][CH2:15]C)=[O:13].C[O-].[Na+]>Cl>[Cl:3][C:4]1[CH:25]=[C:24]([F:26])[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[N:29]([CH3:38])[C:28]2=[O:39])=[CH:22][C:5]=1[O:6][CH2:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[O:10][CH:11]([CH3:17])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 18759635Ethyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate

Product 1

HCID 18759673Methyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionateYield 91.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into 10 ml of methanol was dissolved 0.216 g of ethyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate obtained in the above-described Production Example 3; a catalytic amount of sodium methoxide was added under ice-cooling and stirring and the mixture was stirred for 6 hours at room temperature. The reaction solution was poured into IN hydrochloric acid and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed once with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure to give 0.193 g of methyl 2-[2-({ 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate [Compound 3-1].

Workup

  1. customobtained in the above-described Production Example 3
  2. temperaturecooling
  3. stirringthe mixture was stirred for 6 hours at room temperature
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washwashed once with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9963eb998c94690a7da888384e34624
Source dataset
uspto-grants-2003_12
Patent number
US06664214B1

Reaction notes

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