Boron trifluoride etherate → HCID 178433706, compound

HRID 1736581Notes

Reaction equation

HRID 1736581 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5]2[C:10]=1[C:9](=[O:11])[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[N:6]=2.[O:18]1[CH:22]=[CH:21][CH2:20][CH2:19]1.B(F)(F)F.CCOCC>CN(C=O)C>[O:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[N:4]1[C:5]2=[N:6][C:7]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[N:8][C:9](=[O:11])[C:10]2=[C:2]([CH3:1])[NH:3]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 709342,3-DihydrofuranHCID 19432796HCID 19432796, compound

Product 1

HCID 178433706HCID 178433706, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-6-(4-pyridyl)-pyrazolo[3,4-d]-pyrimidin-4-one (2.3 g, 0.01 mol), DMF (50 ml) and 2,3-dihydrofuran (14.0 g, 0.20 mol) was stirred at 0° C. for 10 minutes and BF3.Et2O (1.5 ml, 0.012 mol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 108 hours. The reaction was quenched with concentrated ammonium hydroxide until pH of 7.5 and the resulting precipitate was collected by filtration. The solid residue was taken up in isopropanol (200 ml), heated to reflux and filtered to remove insoluble material. Concentration of the filtrate to 75 ml and cooling caused precipitation of the product. The product was collected by filtration and washed with ether to afford 1.1 g (37%) of 1-(2-tetrahydrofuranyl)-3-methyl-6-(4-pyridyl)-pyrazolo-[3,4-d]pyrimidin-4-one as a white powder, m.p. 268°-9° C. when dried at 70° C. in high vacuum.

Workup

  1. customThe reaction was quenched with concentrated ammonium hydroxide until pH of 7.5
  2. filtrationthe resulting precipitate was collected by filtration
  3. temperatureheated
  4. temperatureto reflux
  5. filtrationfiltered
  6. customto remove insoluble material
  7. temperatureConcentration of the filtrate to 75 ml and cooling
  8. customprecipitation of the product
  9. filtrationThe product was collected by filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-90d1c1864021482d82bf2d83d9f2843f
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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