Lithium Hydroxide → 3-bromo-7-[(tert-butoxy)carbonyl]-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid

HRID 535917Notes

Reaction equation

HRID 535917 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([O:20]C)=[O:19])[N:3]=1.[Li+].[OH-]>CO.O>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([OH:20])=[O:19])[N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 576351407-(tert-Butyl) 1-methyl 3-bromo-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate

Product 1

HCID 576354283-bromo-7-[(tert-butoxy)carbonyl]-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The product Intermediate 1H (0.85 g, 2.36 mmol) was dissolved in methanol (50 mL) and LiOH (0.79 g, 18.88 mmol) in water (10 mL) was added. The resulting solution was stirred at 50° C. overnight. The reaction mixture was concentrated, cooled on ice and brought to pH 3 using 1N HCl. The resulting white precipitate was filtered, washed with water and air dried to give the desired acid Intermediate 1I as a white solid (0.62 g, 76%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. temperaturecooled on ice
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-d70789213c064bafb128cab904bb2685
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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