Boron tribromide → 2,6-Dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)phenol

HRID 403463Notes

Reaction equation

HRID 403463 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:23][CH3:24])[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH3:22])[C:17]=3[N:18]=2)=[CH:5][C:4]=1[CH3:25].B(Br)(Br)Br>ClCCl>[CH3:9][C:8]1[CH:7]=[C:6]([C:10]2[O:11][C:12]3[N:13]=[C:14]([S:23][CH3:24])[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH3:22])[C:17]=3[N:18]=2)[CH:5]=[C:4]([CH3:25])[C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 672941732-(4-Methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidine

Product 1

HCID 1363898662,6-Dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)phenolYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.5 g of 2-(4-methoxy-3,5-dimethyl-phenyl)-5-methylsulfanyl-7-propoxy-oxazolo[5,4-d]pyrimidine in 50 ml of dichloromethane 0.70 ml of boron tribromide were added slowly at −20° C. After 1 h at −20° C. and 2 h at room temperature, the mixture was quenched by addition of a saturated aqueous sodium hydrogencarbonate solution while maintaining a temperature below 5° C. The phases were separated, and then the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried and concentrated in vacuo. 2.0 g of the title compound were obtained.

Workup

  1. custom2 h at room temperature, the mixture was quenched by addition of a saturated aqueous sodium hydrogencarbonate solution
  2. temperaturewhile maintaining a temperature below 5° C
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. customThe combined organic phases were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-868c79f9033848d090c71879b9b7408f
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Reaction notes

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