Lithium Hydroxide → HCID 67436947, compound

HRID 521376Notes

Reaction equation

HRID 521376 reaction equation
[Li+].[OH-].[CH3:3][C@H:4]1[C:12]2[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH2:6][CH2:5]1>O.C1COCC1>[CH3:3][C@H:4]1[C:12]2[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[N:10][CH:9]=[N:8][C:7]=2[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67437248HCID 67437248, compound

Product 1

HCID 67436947HCID 67436947, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (64 mg, 2.68 mmol) in H2O (10 mL) was added to a solution of (R)-methyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzoate (359 mg, 1.34 mmol) in THF (6 mL) at 0° C. The mixture was allowed to warm up to room temperature and stirred overnight. The volatile solvent was removed in vacuo. The aqueous layer was acidified with 1N HCl to a pH of 3. A solid precipitated, and was collected by filtration, washed with ether, and dried in vacuo to give (R)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzoic acid as a solid (306 mg, 90%).

Workup

  1. customThe volatile solvent was removed in vacuo
  2. customA solid precipitated
  3. filtrationwas collected by filtration
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-43fa8d3346434b02833229a50291b6de
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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