Lithium hydroxide, monohydrate → HCID 178524863, compound

HRID 2169273Notes

Reaction equation

HRID 2169273 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([C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O[Li].O>O1CCCC1>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2([C:29]3[CH:30]=[CH:31][C:32]([Br:35])=[CH:33][CH:34]=3)[CH2:25][CH2:26][CH2:27][CH2:28]2)=[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 178450803HCID 178450803, compound

Product 1

HCID 178524863HCID 178524863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(4-bromophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (230) (7.9 g, 14.64 mmol) in tetrahydrofuran (200 mL) was added an aqueous solution (100 mL) of LiOH.H2O (6.15 g, 146.44 mmol). The resulting mixture was refluxed for 16 h. After completion of the reaction the organic solvent was removed on a rotary evaporator and water (30 mL) was added. The aqueous solution was acidified (pH 5) with concentrated HCl at 0° C. to give a white solid which was filtered off. The solid residue was triturated in diethyl ether and filtered. After drying, 5-benzyloxy-2-[1-(4-bromophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (231) was obtained (6.3 g, 89%) as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 16 h
  2. customAfter completion of the reaction the organic solvent
  3. customwas removed on a rotary evaporator and water (30 mL)
  4. additionwas added
  5. customat 0° C.
  6. customto give a white solid which
  7. filtrationwas filtered off
  8. customThe solid residue was triturated in diethyl ether
  9. filtrationfiltered
  10. customAfter drying

Sources & evidence

ORD record
ord-359eeb042d064f3bb02f7901535f5293
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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