Lithium Hydroxide → 2-(5-Cyano-7-isopropyl-1,3-benzoxazol-2yl)pyrimidine-5-carboxylic acid

HRID 2093621Notes

Reaction equation

HRID 2093621 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[O:12][C:13]3[C:19]([CH:20]([CH3:22])[CH3:21])=[CH:18][C:17]([C:23]#[N:24])=[CH:16][C:14]=3[N:15]=2)=[N:9][CH:10]=1)=[O:4].[OH-].[Li+]>O1CCCC1>[C:23]([C:17]1[CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:13]2[O:12][C:11]([C:8]3[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=3)=[N:15][C:14]=2[CH:16]=1)#[N:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68725848HCID 68725848, compound

Product 1

HCID 687254962-(5-Cyano-7-isopropyl-1,3-benzoxazol-2yl)pyrimidine-5-carboxylic acidYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl-2-(5-cyano-7-isopropyl-1,3-benzoxazol-2yl)pyrimidine-5-carboxylate (429 mg, 1.332 mmol) in tetrahydrofuran (30 ml) was added 1N lithium hydroxide (1.466 ml) dropwise at 60° C. The reaction mixture was stirred at room temperature for 4 h, and then the solution was concentrated and the residue was partitioned between ethyl acetate and water. The aqueous layer was acidified with 1N HCl to pH=4˜5. The white solid was filtered and dissolved in a mixture of dichloromethane and methanol (9:1). This solution was dried over magnesium sulfate and then concentrated to provide the title compound (74 mg) as a yellow solid. Mass spectrum (ESI) 308.8 (M+1). 1H NMR (500 MHz, DMSO) δ 9.45 (s, 2H), 8.42 (s, 1H), 7.92 (s, 1H), 3.20˜3.60 (m, 1H, overlapped with H2O peak), 1.41 (s, 6H).

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. filtrationThe white solid was filtered
  4. dissolutiondissolved in a mixture of dichloromethane and methanol (9:1)
  5. dry with materialThis solution was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-26a61d127cdf40a98766dec182990dee
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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