Acetic Acid → isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

HRID 2248559ノート

反応式

HRID 2248559 の反応式
C[O-].[Na+].[Cl:4][C:5]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=[C:19]2Cl)=[CH:13][C:6]=1[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[C:30](O)(=[O:32])C>CO>[Cl:4][C:5]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]=[C:19]2[O:32][CH3:30])=[CH:13][C:6]=1[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 19994245isopropyl 2-chloro-5-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate

生成物 1

HCID 19994237isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

51.3 ml of a 2N solution of sodium methylate in methanol are added dropwise while stirring and cooling at 0° C. during 5 minutes to a solution of 42.4 g of isopropyl 2-chloro-5-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate in 100 ml of absolute methanol. The reaction mixture is stirred at 0° C. for 10 minutes and adjusted to about pH 4 with concentrated acetic acid. Subsequently, the reaction mixture is evaporated to dryness under reduced pressure. The residue is dissolved in 300 ml of diethyl ether and the solution is washed twice with 100 ml of water each time. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a silica gel column using n-hexane/diethyl ether (3:1) as the eluent and is subsequently recrystallized from n-hexane/diethyl ether. There is obtained isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate, m.p. 121°-123° C.

後処理

  1. stirringThe reaction mixture is stirred at 0° C. for 10 minutes
  2. customSubsequently, the reaction mixture is evaporated to dryness under reduced pressure
  3. dissolutionThe residue is dissolved in 300 ml of diethyl ether
  4. washthe solution is washed twice with 100 ml of water each time
  5. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  6. customevaporated to dryness
  7. customThe residue is purified by chromatography on a silica gel column
  8. customis subsequently recrystallized from n-hexane/diethyl ether

出典と根拠

ORDレコード
ord-dcfc5bc49c574c28ba2478ca122be3bf
出典データセット
uspto-grants-1991_08
特許番号
US05041156

反応ノート

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