Acetonitrile → 6-piperazin-1-yl-3H-pyrimidin-4-one

HRID 1993404Notes

Reaction equation

HRID 1993404 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:18]=[CH:19][NH:20][C:21](=[O:23])[CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(#N)C>[Pd].C(O)C>[N:14]1([C:17]2[N:18]=[CH:19][NH:20][C:21](=[O:23])[CH:22]=2)[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 1361025684-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid benzyl ester2×

Product 1

HCID 1361025406-piperazin-1-yl-3H-pyrimidin-4-oneYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 4-(6-oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid benzyl ester (Intermediate 3; 2.00 g, 7.14 mmol) and a catalytic amount of 10% palladium on carbon in ethanol (300 mL) was hydrogenated at atmospheric temperature and pressure. The starting material is not readily soluble in ethanol so it is clearly visible. After 6 h, the amount of starting material was significantly reduced. Hydrogenation was continued overnight, and a large amount of solid was present. Acetonitrile (300 mL) was added and the mixture was heated to dissolve the solid. The catalyst was filtered off using Celite, and the solvent was evaporated from the filtrate to give 6-piperazin-1-yl-3H-pyrimidin-4-one (820 mg, 64%) as a white solid.

Workup

  1. waitHydrogenation was continued overnight
  2. temperaturethe mixture was heated
  3. dissolutionto dissolve the solid
  4. filtrationThe catalyst was filtered off
  5. customthe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-b8f8fcf0438f4e51b3447ea3079d4210
Source dataset
uspto-grants-2010_01
Patent number
US07652013B2

Reaction notes

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