Triacetoxyperiodinane → Tert-butyl 5-(2,4-dichlorophenyl)-2-formyl-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

HRID 1868472Notes

Reaction equation

HRID 1868472 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([CH2:18][OH:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([CH:18]=[O:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57982523Tert-butyl 5-(2,4-dichlorophenyl)-2-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

Product 1

HCID 57982513Tert-butyl 5-(2,4-dichlorophenyl)-2-formyl-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude tert-butyl 5-(2,4-dichlorophenyl)-2-(hydroxymethyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (400 mg) in CH2Cl2 (6 mL) was added Dess-Martin periodinane (605 mg, 1.43 mmol). After 2 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with satd aq NaHCO3 and brine prior to drying over MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl 5-(2,4-dichlorophenyl)-2-formyl-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (90 mg, 41% for the two steps) as a light yellow solid.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NaHCO3 and brine
  4. dry with materialto drying over MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography

Sources & evidence

ORD record
ord-e1195e51536148c48aca9236c6e9f585
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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