Water → HCID 67717838, compound

HRID 1290641Notes

Reaction equation

HRID 1290641 reaction equation
B(Br)(Br)Br.C[O:6][C:7]([C:10]1[O:11][C:12]2[C:18]([N:19]3[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]3=[O:31])=[C:17]([F:32])[CH:16]=[C:15]([Cl:33])[C:13]=2[N:14]=1)([CH3:9])[CH3:8].O>C(Cl)Cl>[OH:6][C:7]([C:10]1[O:11][C:12]2[C:18]([N:19]3[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]3=[O:31])=[C:17]([F:32])[CH:16]=[C:15]([Cl:33])[C:13]=2[N:14]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67717542HCID 67717542, compound

Product 1

HCID 67717838HCID 67717838, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere a stirred solution of 3.8 mL (3.8 mmole) of 1M boron tribromide (in methylene chloride) in 50 mL of methylene chloride was cooled to about -40° C., and a solution of 0.6 gram (2.6 mmole) of 3-[2-(1-methoxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione in 50 mL of methylene chloride was added dropwise at such a rate as to maintain the reaction mixture temperature below -30° C. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours. At the conclusion of this period the reaction mixture was poured into water and thoroughly extracted with methylene chloride. The combined extracts were washed with an aqueous saturated sodium chloride solution, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a brown oil, which was subjected to column chromatography on silica gel. Elution was with 1:4 ethyl acetate to heptane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 3-[2-(1-hydroxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto maintain the reaction mixture temperature below -30° C
  2. additionUpon completion of the addition the reaction mixture
  3. extractionthoroughly extracted with methylene chloride
  4. washThe combined extracts were washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a brown oil, which
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-686dacd84fa34035bc54bc926000ac59
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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