Potassium Carbonate → 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

HRID 432558ノート

反応式

HRID 432558 の反応式
[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(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:44]=[CH:43][CH:42]=[CH:41][C:32]=1[O:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36]>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][CH2:30][C:31]1[CH:44]=[CH:43][CH:42]=[CH:41][C:32]=1[O:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 11808300Ethyl 2-(2-bromomethylphenoxy)propionate

生成物 1

HCID 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収率 72.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Into 10 ml of N,N-dimethylformamide was dissolved 0.3 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenol; 0.159 g of anhydrous potassium carbonate was added; 0.305 g of ethyl 2-[2-(bromomethyl)phenoxy]propionate was added at room temperature under stirring and the mixture was stirred overnight at room temperature. The reaction solution was poured into a mixture of ice and a saturated aqueous ammonium chloride solution and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed once with a saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution in turn, dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 0.35 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 [Compound 3-2].

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. additionThe reaction solution was poured into a mixture of ice
  3. extractiona saturated aqueous ammonium chloride solution and the mixture was extracted twice with ethyl acetate
  4. washwashed once with a saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution in turn
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9b681321d8134aeca590c3f6c83db852
出典データセット
uspto-grants-2003_12
特許番号
US06664214B1

反応ノート

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