Ethyl Acetate → HCID 178457452, compound

HRID 2169411Notes

Reaction equation

HRID 2169411 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13])(C(C)(C)C)(C)C.C(OCC)(=O)C>O1CCCC1.Cl.CCCCCC>[OH:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 178457486HCID 178457486, compound

Product 1

HCID 178457452HCID 178457452, compoundYield 85.45%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (378) (5.7 g, 8.80 mmol) in tetrahydrofuran (50 mL), 1N HCl (15 mL) was added and the reaction mixture was stirred for 1 h at room temperature while silica thin layer chromatography was performed (70% ethyl acetate in hexane; Rf=0.2). After completion of the reaction, volatiles were removed and the residue was diluted with water (30 mL) and adjusted to pH 8 using NaHCO3. The aqueous mixture was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried and concentrated. The resulting residue was purified by column over normal silica gel (100-200) to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylicacid(2-hydroxyethyl)-isopropylamide (379) (4.02 g, 85.45%) as a white solid.

Workup

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue was diluted with water (30 mL)
  4. extractionThe aqueous mixture was extracted with ethyl acetate (2×150 mL)
  5. customthe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column over normal silica gel (100-200)

Sources & evidence

ORD record
ord-446fdd30242542928f4fca99cb289326
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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