Methyl Ethyl Ketone → Ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate

HRID 1381583노트

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HRID 1381583 반응식
[C:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([O:16][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:13]=[CH:12][N:11]=2)=[C:6]([CH2:19][CH2:20][CH3:21])[C:5]=1[OH:22])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1784395372-[(4-Acetyl-3-hydroxy-2-propylbenzyl)thio]-4-hydroxypyrimidine

생성물 1

HCID 14053136Ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4-yl]oxy]acetate수율 78.7%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

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온도
60 °C

실험 절차

To a mixture of 0.06 g of 2-[(4-acetyl-3-hydroxy-2propylbenzyl)thio]-4-hydroxypyrimidine obtained in Example 14, 0.06 g of ethyl bromoacetate, 0.04 g of anhydrous potassium carbonate and 3 ml of methyl ethyl ketone was added a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred at 60° C. for 1 hour. Water was added to the reaction mixture. The resultant mixture was extracted with ethyl acetate. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (6:1) gave 0.06 g of ethyl [[2-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-pyrimidin-4yl]oxy]acetate.

후처리

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. washElution
  5. additionwith a mixture of hexane-ethyl acetate (6:1)

출처 및 근거

ORD 기록
ord-a8e913dedf7b4d2b972a644efa4e820d
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803211

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