Ethyl Acetate → HCID 178524880, compound

HRID 2169409Notes

Reaction equation

HRID 2169409 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[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])[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[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])=[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 178450820HCID 178450820, compound

Product 1

HCID 178524880HCID 178524880, compoundYield 94.7%

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (376) (14 g, 27.723 mmol) in tetrahydrofuran-water (15:7, 220 mL) was added LiOH.H2O (11.644 g, 277.228 mmol). The reaction mixture was refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.1). After completion of the reaction, all volatiles were removed and the residue was diluted with water (50 mL) and neutralized to pH 7 with 1N HCl. The mixture was filtered and the resulting solid was dried to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (377) (11.8 g, 94.65%) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h while silica thin layer chromatography
  2. customAfter completion of the reaction
  3. customall volatiles were removed
  4. additionthe residue was diluted with water (50 mL)
  5. filtrationThe mixture was filtered
  6. customthe resulting solid was dried

Sources & evidence

ORD record
ord-56e78e9572824edbace6c0818f3c002e
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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