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Triacetoxyperiodinane → Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetate

HRID 472833
Notes
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Reaction equation

HRID 472833 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86670273Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

Product 1

HCID 86670275Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetateYield 76.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (5 g, 13.65 mmol) in CH2Cl2 (20 mL) was added Dess-MartinPeriodinane (6.37 g, 15.02 mmol) and the reaction mixture was stirred at room temp for 1 h. The reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was washed with saturated NaHCO3 solution (100 mL) and dried (Na2SO4). The solvent was evaporated and the residue was purified by a quick silica gel chromatography to afford (3.8 g, 76%) of the title compound. 1H NMR (500 MHz, CHLOROFORM-d) δ 8.10-7.98 (m, 1H), 7.89 (td, J=4.4, 1.5 Hz, 1H), 7.51-7.36 (m, 2H), 7.00 (s, 1H), 4.00 (s, 3H), 2.62 (s, 3H).

Workup

  1. washThe organic layer was washed with saturated NaHCO3 solution (100 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated
  4. customthe residue was purified by a quick silica gel chromatography

Sources & evidence

ORD record
ord-380cca842d714eb6827abbaae20a531a
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633200B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes