Boron tribromide → HCID 178516247, compound

HRID 1602260Notes

Reaction equation

HRID 1602260 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[CH:17][N:16]=[C:15]3[NH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=4)[C:14]=23)[CH:9]=[CH:10][CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[CH:17][N:16]=[C:15]3[NH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=4)[C:14]=23)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178492223HCID 178492223, compound

Product 1

HCID 178516247HCID 178516247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Under a nitrogen atmosphere, a solution of 5 ml (51.9 mmol) of boron tribromide in 20 ml of methylene chloride is added dropwise over a period of 30 minutes to a suspension, cooled to 0° C., of 5 g (13.63 mmol) of 4-(3-chloro-phenylamino)-3-(4-methoxy-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 100 ml of methylene chloride. The reaction mixture is stirred at 20° C. for 14 hours and then filtered and the filter residue is digested for 1/2 hour at RT in 85 ml of water. After filtering, the filter residue is partitioned between 50 ml of saturated sodium hydrogen carbonate solution, 50 ml of water and 135 ml of THF. The organic phase is separated off, the aqueous phase is extracted again with 35 ml of THF, the combined THF extracts are washed with brine and the organic phase is dried over sodium sulfate and concentration by evaporation is carried out in vacuo. The crystalline residue is digested in 65 ml of boiling ethyl acetate, cooled to RT and filtered, yielding the crude title compound. Recrystallization of a sample from ethyl acetate yields the pure title compound; m.p. >260° C.; TLC-Rf =0.54 (toluene/isopropanol/conc. ammonia [70:29:1]).

Workup

  1. filtrationfiltered
  2. waitthe filter residue is digested for 1/2 hour at RT in 85 ml of water
  3. filtrationAfter filtering
  4. customthe filter residue is partitioned between 50 ml of saturated sodium hydrogen carbonate solution, 50 ml of water and 135 ml of THF
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted again with 35 ml of THF
  7. washthe combined THF extracts are washed with brine
  8. dry with materialthe organic phase is dried over sodium sulfate and concentration by evaporation
  9. temperaturecooled to RT
  10. filtrationfiltered
  11. customyielding the crude title compound
  12. customRecrystallization of a sample from ethyl acetate

Sources & evidence

ORD record
ord-2acdbe4241a24cd8a084e2d87b94dc13
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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