Water → HCID 178524875, compound

HRID 2169250Notes

Reaction equation

HRID 2169250 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]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[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:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[Cl:36])[CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:11][C:12]=1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 178450815HCID 178450815, compound

Product 1

HCID 178524875HCID 178524875, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (204) (2.0 g, 3.788 mmol) in tetrahydrofuran-H2O (2:1) (30 mL) Li(OH).H2O (1.591 g, 37.88 mmol) was added, then the reaction mixture was stirred under reflux for 16 h. Silica thin layer chromatography was performed (40% ethyl acetate in hexane, Rf=0.1). After completion of the reaction, volatiles were removed, the reaction mixture was diluted with water, the pH was adjusted to pH ˜7 with 1N HCl, then the reaction mixture was extracted with ethyl acetate. The organic part was dried with Na2SO4, then concentrated to get pure 5-benzyloxy-2-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (205) (1.3 g, 72.5%) as a white solid.

Workup

  1. temperatureunder reflux for 16 h
  2. customAfter completion of the reaction, volatiles
  3. customwere removed
  4. additionthe reaction mixture was diluted with water
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe organic part was dried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c86fbbb53594578a26687c84a81775b
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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