Lithium hydroxide, monohydrate → 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylic acid

HRID 1930388ノート

反応式

HRID 1930388 の反応式
C(O)C.O.O1CCOCC1.[CH3:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[CH:22]=[CH:21]3)[C:15]([C:28]([O:30]CC)=[O:29])=[CH:14][N:13]=1.O.[OH-].[Li+]>C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[CH:22]=[CH:21]3)[C:15]([C:28]([OH:30])=[O:29])=[CH:14][N:13]=1

参加物

6

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 69037048ethyl 2-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylateHCID 69104347Dioxane ethanol water

生成物 1

HCID 690369112-methyl-4-(1-methyl-1H-indol-5-yl)pyrimidine-5-carboxylic acid収率 37.3%

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a mix of ethanol:water:dioxane (1:1:1, 9 mL) was placed ethyl 2-methyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylate (391 mg, 1.324 mmol) and lithium hydroxide hydrate (222 mg, 5.30 mmol). The mix stirred at RT overnight. The mix was diluted with ethyl acetate (25 mL) and 5% citric acid (20 mL). The organic phase was separated, washed with brine (20 mL) and dried over sodium sulfate. The solvent was evaporated at reduced pressure to give 2-methyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylic acid as a tan solid (132 mg, 37% yield). MS (ESI) m/z: 268.0 (M+H+).

後処理

  1. customThe organic phase was separated
  2. washwashed with brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated at reduced pressure

出典と根拠

ORDレコード
ord-9589b9b47fe84d4991e60260722f9d8e
出典データセット
uspto-grants-2012_05
特許番号
US08188113B2

反応ノート

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