Lithium hydroxide, monohydrate → HCID 178524879, compound

HRID 2169216Notes

Reaction equation

HRID 2169216 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]=[C:26]([Cl:30])[C:25]=2[Cl:31])[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]=[C:26]([Cl:30])[C:25]=2[Cl:31])=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178450819HCID 178450819, compound

Product 1

HCID 178524879HCID 178524879, compoundYield 85.32%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (130) (10 g, 21.69 mmol) in a mixture of tetrahydrofuran-water (2:1, 90 mL) was added lithium hydroxide, monohydrate (4.55 g, 108.42 mmol). 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 residue was washed with ethyl acetate to remove non-acidic impurities. The separated aqueous part was acidified with 2(N)HCl to bring the pH to approx. 5 to 6. The acidified aqueous part was extracted with dichloromethane, the separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (131) (7.5 g, 85.32%) 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 residue was washed with ethyl acetate
  6. customto remove non-acidic impurities
  7. extractionThe acidified aqueous part was extracted with dichloromethane
  8. dry with materialthe separated organic part was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9a48c62d9a94c409dfa168e94de8e21
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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