Lithium hydroxide, monohydrate → HCID 178524878, compound

HRID 2169129Notes

Reaction equation

HRID 2169129 reaction equation
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:9]=1)=[O:7])(C)(C)C.O.[OH-].[Li+]>O1CCCC1.O>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178450818HCID 178450818, compound

Product 1

HCID 178524878HCID 178524878, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (6-01) (5 g, 10.68 mmol) in a mixture of tetrahydrofuran and water (2:1, 90 mL) was added lithium hydroxide, monohydrate (2.2 g, 53.4 mml). The mixture was refluxed for 18 h. After completion of the reaction, the volume was reduced by evaporation as much as possible, water was added and the mixture was washed with ethyl acetate to remove non-acidic impurities. The separated aqueous part was acidified with 1N HCl to bring the pH to about 5 to 6. The acidified aqueous part was extracted with dichloromethane to get 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid (7-01) (3 g, 68%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. customAfter completion of the reaction
  3. customthe volume was reduced by evaporation as much as possible, water
  4. additionwas added
  5. washthe mixture was washed with ethyl acetate
  6. customto remove non-acidic impurities
  7. extractionThe acidified aqueous part was extracted with dichloromethane

Sources & evidence

ORD record
ord-51dfefe0057f4b48aa7136697c38f25e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…