Ethyl Acetate → HCID 178524873, compound

HRID 2169467Notes

Reaction equation

HRID 2169467 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][CH:32]=[CH:31][N:30]=3)[CH2:28][CH2:27][CH2:26][CH2:25]2)[N:9]=1)=[O:7])(C)(C)C.O[Li].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]=[CH:33][CH:32]=[CH:31][N:30]=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

6

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450813HCID 178450813, compound

Product 1

HCID 178524873HCID 178524873, compoundYield 87.3%

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (436) (1.2 g, 2.60 mmol) in tetrahydrofuran-water (2:1; 24 mL), LiOH.H2O (1.09 g, 26.03 mmol) was added, refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.1). From the reaction mixture volatiles were removed and the residue was diluted with water (20 mL). Thereafter, the pH of this mixture was adjusted to 7 with 1N aqueous HCl. The resulting precipitate was filtered and dried. The obtained solid was triturated with ether to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (920 mg, 87%) as a white solid.

Workup

  1. temperaturerefluxed for 16 h while silica thin layer chromatography
  2. customFrom the reaction mixture volatiles were removed
  3. additionthe residue was diluted with water (20 mL)
  4. filtrationThe resulting precipitate was filtered
  5. customdried
  6. customThe obtained solid was triturated with ether

Sources & evidence

ORD record
ord-d74a4fddb62b4dacbe7c2d5579154d7a
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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