Triacetoxyperiodinane → HCID 89522294, compound

HRID 529714Notes

Reaction equation

HRID 529714 reaction equation
[Br:1][C:2]1[C:3]([CH2:11][OH:12])=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH:11]=[O:12])=[N:4][C:5]([N:8]([CH3:9])[CH3:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89522331HCID 89522331, compound

Product 1

HCID 89522294HCID 89522294, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [5-bromo-2-(dimethylamino)pyrimidin-4-yl]methanol (19 g, 82 mmol) in DCM (10 mL) was added Dess-Martin periodinane (41.7 g, 98 mmol) at room temperature. The reaction was stirred overnight and the reaction was diluted with hexanes, filtered and was concentrated before purification by column chromatography to yield 5-bromo-2-(dimethylamino)pyrimidine-4-carbaldehyde (10 g, 43.5 mmol). 1H NMR (500 MHz, CDCl3) δ 9.95 (s, 1H), 8.52 (s, 1H), 3.24 (s, 6H).

Workup

  1. filtrationfiltered
  2. concentrationwas concentrated before purification by column chromatography

Sources & evidence

ORD record
ord-255c4a5f4b2e42e5be4cb08d4ae43876
Source dataset
uspto-grants-2016_05
Patent number
US09346825B2

Reaction notes

Loading…