Triacetoxyperiodinane → HCID 86663779, compound

HRID 405985Notes

Reaction equation

HRID 405985 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH2:13][OH:14].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66831374HCID 66831374, compound

Product 1

HCID 86663779HCID 86663779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-bromo-2-(hydroxymethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (1 equiv) and NaHCO3 (6 equiv) in DCM was added Dess-Martin periodinane (1.5 equiv) at rt with stirring. The reaction mixture was stirred at rt for 3 h, monitered by MS and TLC. The mixture was diluted with DCM and filtered off through Celite™, and the filtrate was cond under vacuum. The crude was purified by silica gel column chromatography using 80% EtOAc in hexane as eluent to give the 3-bromo-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carbaldehyde as a yellowish solid: 1HNMR (400 MHz, DMSO-d6): δ10.12 (s,1H), 9.00-9.01 (dd,1H), 8.03-8.12 (m,1H), 7.89-7.91 (dd,1H), 7.50-7.54 (m,1H).

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 h
  2. filtrationfiltered off through Celite™
  3. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6f00d07006264a57a5cc6a9b098a4250
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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