Ammonium formate → 4-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 589950Notes

Reaction equation

HRID 589950 reaction equation
C([N:8]1[CH2:15][CH2:14][N:13]([C:16]2[C:17]3[CH:24]=[CH:23][NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:12][C:9]21[CH2:11][CH2:10]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:11]1[C:9]2([CH2:12][N:13]([C:16]3[C:17]4[CH:24]=[CH:23][NH:22][C:18]=4[N:19]=[CH:20][N:21]=3)[CH2:14][CH2:15][NH:8]2)[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 668882384-(4-benzyl-4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine2×

Product 1

HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 165.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-(4-benzyl-4,7-diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine (intermediate 22) (50 g, 78.36 mmol) in MeOH, was added 10% Pd/C (20 g) and HCOONH4 (98 g, 783.69 mmol) and the reaction mixture was heated to reflux for 30 min. The reaction mixture was filtered through celite bed and washed with MeOH and concentrated under reduced pressure. The crude compound was treated with 50% NaOH solution (200 ml) and stirred for 15 min and solid was obtained by filtration. And the solid was wash with 50 ml of water and dried under vacuum. The crude compound (33 g) in acetone (10 times) was heated to reflux for 30 min. The reaction mixture was cooled and filtered and the solid was washed with acetone to afford the title compound as a solid (29.78 g, 83%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationThe reaction mixture was filtered through celite bed
  4. washwashed with MeOH
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude compound was treated with 50% NaOH solution (200 ml)
  7. customsolid was obtained by filtration
  8. washAnd the solid was wash with 50 ml of water
  9. customdried under vacuum
  10. temperatureThe crude compound (33 g) in acetone (10 times) was heated
  11. temperatureto reflux for 30 min
  12. temperatureThe reaction mixture was cooled
  13. filtrationfiltered
  14. washthe solid was washed with acetone

Sources & evidence

ORD record
ord-d7354443933e41e584322ec1856049da
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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