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

HRID 1930388Notes

Reaction equation

HRID 1930388 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-9589b9b47fe84d4991e60260722f9d8e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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