Boron tribromide → 4-(7-Chloro-5-methylsulfanyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol

HRID 633615Notes

Reaction equation

HRID 633615 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[C:7]2[N:16]=[C:15]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([O:24]C)=[C:19]([CH3:26])[CH:18]=3)[O:14][C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:5][C:6]1[C:7]2[N:16]=[C:15]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH3:26])[CH:18]=3)[O:14][C:8]=2[N:9]=[C:10]([S:12][CH3:13])[N:11]=1

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 71743137HCID 71743137, compound

Product 1

HCID 1364132354-(7-Chloro-5-methylsulfanyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −20° C., 5.30 g of boron tribromide were added dropwise with stirring to a solution of 6.72 g of 7-chloro-2-(4-methoxy-3,5-dimethylphenyl)-5-methylsulfanyloxazolo[5,4-d]pyrimidine in 140 ml of dichloromethane. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours. With ice cooling, another 1.33 g of boron tribromide were then added dropwise. After a further 2 hours, the reaction was once more cooled to −20° C., and sat. aqueous sodium bicarbonate solution was carefully added dropwise. The phases were separated at room temperature. The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diisopropyl ether, filtered off with suction and air-dried. This gave 6.20 g (96%) of the title compound, which was reacted further without any further purification.

Workup

  1. waitAfter a further 2 hours
  2. temperaturethe reaction was once more cooled to −20° C.
  3. customThe phases were separated at room temperature
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationfiltered off with suction
  10. customair-dried
  11. customThis gave 6.20 g (96%) of the title compound, which was reacted further without any further purification

Sources & evidence

ORD record
ord-1808779e1aa64dc39bf65d4e82282f39
Source dataset
uspto-grants-2016_04
Patent number
US09321787B2

Reaction notes

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