Boron trifluoride etherate → HCID 53443879, compound

HRID 1896574Notes

Reaction equation

HRID 1896574 reaction equation
[N:1]1C=NC=N[CH:2]=1.[NH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[N:11]=[CH:10][C:9]=1[C:20](O)=O.B(F)(F)F.CCOCC>CS(C)=O.CCOC(C)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]3=[N:7][CH:2]=[N:1][CH:20]=[C:9]3[CH:10]=[N:11]2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 92621,3,5-TriazineHCID 40570295-Amino-1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 53443879HCID 53443879, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1,3,5-triazine (0.575 g, 7.09 mmol) and 5-amino-1-(4-bromophenyl)-1H-pyrazole-4-carboxylic acid (22A) (2 g, 7.09 mmol) in DMSO (30 mL) was added boron trifluoride etherate (1.08 mL, 8.51 mmol). The resulting mixture was heated at 120° C. for 20 hours, cooled, diluted with EtOAc and washed with 1% NaOH and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated with small amount of EtOAc and the precipitate was collected to provide the desired product 1-(4-bromophenyl)-1H-pyrazolo[3,4-d]pyrimidine (22B): 1H NMR (400 MHz, DMSO-D6) δ ppm 9.47 (1H, s), 9.16 (1H, s), 8.68 (1H, s), 8.22 (2H, d), 7.80 (2H, d).

Workup

  1. temperaturecooled
  2. washwashed with 1% NaOH and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with small amount of EtOAc
  6. customthe precipitate was collected

Sources & evidence

ORD record
ord-b8f93a592a0149feb3b37cdfa25c3c64
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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