p-Toluenesulfonic acid → 6-piperazin-1-yl-3H-pyrimidin-4-one

HRID 1993403Notes

Reaction equation

HRID 1993403 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[CH:16][NH:17][C:18](=[O:20])[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[N:11]1([C:14]2[N:15]=[CH:16][NH:17][C:18](=[O:20])[CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 1361025614-(6-Oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1361025406-piperazin-1-yl-3H-pyrimidin-4-oneYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(6-oxo-1,6-dihydro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (13.5 g, 48.2 mmol) in dichloromethane (200 mL) was added MP-TsOH (available from Aldrich; 81.0 g). The reaction was shaken at room temperature for 4 days. The crude reaction mixture was filtered and the resin was washed with methanol (460 mL). The desired product was eluted from the resin with 2M ammonia in methanol (460 mL) to give 6-piperazin-1-yl-3H-pyrimidin-4-one (8.4 g, 90%). LCMS Purity=96% (Rt=0.22 in the solvent front). 1H NMR (d6-DMSO) δ 7.75 (s, 1H), 5.10 (s, 1H), 2.60-2.42 (m, 4H), 2.38-2.25 (m, 4H).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. washthe resin was washed with methanol (460 mL)
  4. washThe desired product was eluted from the resin with 2M ammonia in methanol (460 mL)

Sources & evidence

ORD record
ord-9b7ad11a972941738e9479dfbe85a909
Source dataset
uspto-grants-2010_01
Patent number
US07652013B2

Reaction notes

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