Benzyl 3-{4-[5-(3-chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylate → 3-{4-[5-(3-Chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylic acid

HRID 1027717Notes

Reaction equation

HRID 1027717 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[O:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:35]=[C:34]([CH3:36])[C:18]([O:19][CH:20]4[CH2:23][CH:22]([C:24]([O:26]CC5C=CC=CC=5)=[O:25])[CH2:21]4)=[C:17]([CH3:37])[CH:16]=3)[O:12][C:10]=2[N:11]=1>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][CH:40]=1)[O:5][C:6]1[N:7]=[CH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:35]=[C:34]([CH3:36])[C:18]([O:19][CH:20]4[CH2:23][CH:22]([C:24]([OH:26])=[O:25])[CH2:21]4)=[C:17]([CH3:37])[CH:16]=3)[O:12][C:10]=2[N:11]=1

Participants

4

Reactant 1

HCID 71225588Benzyl 3-{4-[5-(3-chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylate

Product 1

HCID 712033493-{4-[5-(3-Chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylic acidYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

77 mg of benzyl 3-{4-[5-(3-chlorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}cyclobutanecarboxylate were dissolved in 4.4 ml of ethyl acetate, 2.5 mg of palladium on carbon (5%) were added and the mixture was hydrogenated at 3 bar and room temperature. After 5 h, the catalyst was filtered off. The filtrate was concentrated, and purification by preparative HPLC gave 20 mg (32%) of the title compound.

Workup

  1. customwas hydrogenated at 3 bar and room temperature
  2. filtrationthe catalyst was filtered off
  3. concentrationThe filtrate was concentrated
  4. custompurification by preparative HPLC

Sources & evidence

ORD record
ord-50becb0986f247d1bfb51b74cf2d69a0
Source dataset
uspto-grants-2014_05
Patent number
US08735402B2

Reaction notes

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