Lithium hydroxide, monohydrate → HCID 178524871, compound

HRID 2169360Notes

Reaction equation

HRID 2169360 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]([Cl: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.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([C:29]3[CH:30]=[CH:31][C:32]([Cl: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

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178450811HCID 178450811, compound

Product 1

HCID 178524871HCID 178524871, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (323) (4.82 g, 9.74 mmol) in tetrahydrofuran (90 mL) and water (45 mL) was added LiOH.H2O (4.086 g, 97.37 mmol). The reaction mixture was heated to reflux for 20 h (the reaction was monitored by LC-MS). The tetrahydrofuran was removed in vacuo and the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The aqueous layer was acidified with 1N HCl to about pH 3. A white solid was separated by filtration and dried in vacuo to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (324) (3.47 g, 81%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 h (the reaction
  3. customThe tetrahydrofuran was removed in vacuo
  4. additionthe reaction mixture was diluted with water (100 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. customA white solid was separated by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bccc268f98fc454abcde953ed8a3119d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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