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Acetic Acid → 2-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

HRID 19666
ノート
印刷プレビュー

反応式

HRID 19666 の反応式
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1.C(O)(=O)C>O1CCOCC1.O>[CH3:19][S:18][C:14]1[N:15]=[C:16]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:12][N:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidine

生成物 1

HCID 111838682-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 31275
1,4-Dioxane
溶媒
2 回

反応条件

温度
100 °C

実験手順

Benzyl alcohol (1.3 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 0.74 g) in 12.4 mL of dry dioxane, and the mixture was stirred at 100° C. for 30 min. A solution of 4-chloro-2-(methylthio)pyrimidine (2.0 g) in dry dioxane (8.2 mL) was added dropwise at 50° C. and the mixture was stirred at this temperature for 5 hours. After cooling at room temperature the mixture was acidified with glacial acetic acid, treated with water and extracted with dichloromethane. The organic phases were dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (70 g) eluting with ciclohexane/ethyl acetate from 95/5 to 9/1 to give the title compound as a white solid (1.22 g).

後処理

  1. stirringthe mixture was stirred at this temperature for 5 hours
  2. temperatureAfter cooling at room temperature the mixture
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by a silica SPE cartridge (70 g)
  8. washeluting with ciclohexane/ethyl acetate from 95/5 to 9/1

出典と根拠

ORDレコード
ord-cf272e86264b42c7abe6ebbb6c17ca0d
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07745458B2

反応ノート

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