Triacetoxyperiodinane → HCID 117604155, compound

HRID 921068Notes

Reaction equation

HRID 921068 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([O-:13])=[O:12])[CH:10]=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[CH:15]([OH:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH3:22][C:23](OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]([O:13][CH2:22][CH3:23])=[O:12])[CH:10]=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131734899HCID 131734899, compound

Product 1

HCID 117604155HCID 117604155, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-chloro-6-(2-ethoxy-1-hydroxy-2-oxoethyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (5.9 g 13.81 mmol) in CH2Cl2 (100 mL) was added Dess-Martin (5.86 g, 13.81 mmol) and the resulting mixture was stirred at rt for 1 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with sat. aq. NaHCO3 solution (30 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (5-70% EtOAc/hexane) to afford the desired ethyl 7-chloro-6-(2-ethoxy-2-oxoacetyl)-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (3.5 g, 9.27 mmol, 67.1% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.24 (s, 1H), 4.56-4.43 (m, 4H), 2.63 (s, 3H), 1.50-1.41 (m, 6H). LCMS (M+1)=340.13.

Workup

  1. washwashed with sat. aq. NaHCO3 solution (30 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-70% EtOAc/hexane)

Sources & evidence

ORD record
ord-3177af9acc9c4b67a2df1bda60f7deb3
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

Loading…