Triacetoxyperiodinane → HCID 57526855, compound

HRID 1452627Notes

Reaction equation

HRID 1452627 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([C:17]1[N:22]2[N:23]=[CH:24][CH:25]=[C:21]2[N:20]=[C:19]([Cl:26])[C:18]=1[CH2:27][CH2:28][CH2:29][OH:30])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[N:7]([C:17]1[N:22]2[N:23]=[CH:24][CH:25]=[C:21]2[N:20]=[C:19]([Cl:26])[C:18]=1[CH2:27][CH2:28][CH:29]=[O:30])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57526810HCID 57526810, compound

Product 1

HCID 57526855HCID 57526855, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (1.7 mL) solution containing tert-butyl[5-chloro-6-(3-hydroxypropyl)pyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)carbamate (155 mg, 0.346 mmol), Dess-Martin periodinane (152 mg, 0.381 mmol) was added with ice-cooling, and this mixture was stirred at room temperature for 16 hr. The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified with column chromatography (10 to 20% ethyl acetate-hexane) to obtain the title compound (117 mg, yield 76%).

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified with column chromatography (10 to 20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a60b91a2539c47d4b9bded5718be38fc
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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