Ammonium formate → HCID 18768328, compound

HRID 480025Notes

Reaction equation

HRID 480025 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15](=[O:22])[NH:14][C:13]1=[O:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O1CCCC1.[Pd]>[CH3:1][NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[C:15](=[O:22])[NH:14][C:13]1=[O:23]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 18768333HCID 18768333, compound

Product 1

HCID 18768328HCID 18768328, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.29 g (13.11 mmol) of 1-{3-[benzyl(methyl)amino]propyl}-5,6,7,8-tetrahydro-2,4(1H,3H)-quinazolinedione in a mixture of 50 ml of methanol and 10 ml of tetrahydrofuran is admixed with 5.6 mg of 10% palladium-on-carbon. Over a period of 45 minutes, three portions of in total 8.61 g (136.6 mmol) of ammonium formate are then added. After the addition has ended, the mixture is heated at reflux for 1.5 hours. After cooling, the mixture if filtered through a little kieselguhr and the solvent is removed under reduced pressure. This gives 2.24 g (9.44 mmol, 72% yield) of the product as a colourless solid.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 1.5 hours
  4. temperatureAfter cooling
  5. filtrationthe mixture if filtered through a little kieselguhr
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-743837f77b9f4525be03fec926b330b3
Source dataset
uspto-grants-2003_11
Patent number
US06649618B2

Reaction notes

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