Ethyl Acetate → Ethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)acetate

HRID 2278581ノート

反応式

HRID 2278581 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1.[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22]>C1COCC1>[CH2:25]([O:24][C:21](=[O:23])[CH2:22][C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1)[CH3:26]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 38245092,4-Dichloro-6-methoxypyrimidine

生成物 1

HCID 86699270Ethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-75 °C

実験手順

91.4 ml of 1M lithium bis(trimethylsilyl)amide (THF) are added dropwise to a solution of 7.4 g of 2,4-dichloro-6-methoxypyrimidine and 4.5 ml of ethyl acetate in 100 ml of anhydrous THF cooled to −75° C. in a dry ice/acetone bath. The reaction medium is stirred at −75° C. for one hour. The cooling bath is removed so as to allow the temperature to rise to 22° C. The reaction medium is stirred at 22° C. for one hour. 100 ml of water and 400 ml of ethyl acetate are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure so as to give 9.5 g of (4-chloro-6-methoxypyrimidin-2-yl)acetic acid ethyl ester in the form of an orange oil, the characteristics of which are the following:

後処理

  1. customThe cooling bath is removed so as
  2. customto rise to 22° C
  3. stirringThe reaction medium is stirred at 22° C. for one hour
  4. addition100 ml of water and 400 ml of ethyl acetate are added
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure so as

出典と根拠

ORDレコード
ord-9f2c058dfccb480a84a97f2c9a65b736
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

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