Sodium Methoxide → 2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid

HRID 2110692ノート

反応式

HRID 2110692 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH3:23][O-:24].[Na+]>CO>[CH3:23][O:24][C:7]1[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=1

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 576360902-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester2 回

生成物 1

HCID 576360412-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid収率 64%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A mixture of 2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [650 mg, 2.02 mmol, Intermediate (55)] 5M sodium methoxide in MeOH (20 mL, 10.1 mmol), in MeOH (10 mL) is heated to reflux and stirred for 5 hours. The heating is turned off and the mixture is stirred for 15 hours at room temperature and concentrated by rotary evaporator to remove the solvent. The solid is dissolved in water and the solution is acidified to pH 2 with the addition of 1N hydrochloric acid. Extracted three times with 75 mL EtOAc and concentrated the combined organic extracts to afford 2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid [390 mg, 64%, Intermediate (56)] as a solid. LCMS: RT=1.99 minutes, MS: 304 (M+H).

後処理

  1. temperatureto reflux
  2. stirringthe mixture is stirred for 15 hours at room temperature
  3. concentrationconcentrated by rotary evaporator
  4. customto remove the solvent
  5. dissolutionThe solid is dissolved in water
  6. additionthe solution is acidified to pH 2 with the addition of 1N hydrochloric acid
  7. extractionExtracted three times with 75 mL EtOAc
  8. concentrationconcentrated the combined organic extracts

出典と根拠

ORDレコード
ord-557c665ed4244185a148ed30060b5370
出典データセット
uspto-grants-2009_04
特許番号
US07517889B2

反応ノート

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