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

HRID 81501Notes

Reaction equation

HRID 81501 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2[O:15][C:16]3[N:17]=[C:18]([S:27][CH3:28])[N:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[C:21]=3[N:22]=2)=[CH:9][C:8]=1[CH3:29]>ClCCl>[CH3:13][C:12]1[CH:11]=[C:10]([C:14]2[O:15][C:16]3[N:17]=[C:18]([S:27][CH3:28])[N:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[C:21]=3[N:22]=2)[CH:9]=[C:8]([CH3:29])[C:7]=1[OH:6]

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)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −20° C., 0.70 ml of boron tribromide was added slowly to a solution of 2.5 g of 2-(4-methoxy-3,5-dimethylphenyl)-5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidine in 50 ml of dichloromethane. After 1 h at −20° C. and 2 h at room temperature, the mixture was quenched by addition of saturated aqueous sodium bicarbonate solution, with the temperature being kept below 5° C. After phase separation, the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried and concentrated under reduced pressure. This gave 2.0 g of the title compound.

Workup

  1. custom2 h at room temperature, the mixture was quenched by addition of saturated aqueous sodium bicarbonate solution, with the temperature
  2. custombeing kept below 5° C
  3. customAfter phase separation
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. customThe combined organic phases were dried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a180a50dfd641e38944f79155065fa2
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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