2-Methyl-2-thiopseudourea → 2-(4-Methylpiperazin-1-yl)-5-nitropyrimidine

HRID 2236414Notes

Reaction equation

HRID 2236414 reaction equation
[N+:1]([CH:4]([CH:7]=O)[CH:5]=O)([O-:3])=[O:2].CS[C:11](=[NH:13])[NH2:12].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:11]2[N:13]=[CH:7][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:12]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 51422-Methyl-2-thiopseudoureaHCID 531671-MethylpiperazineHCID 313475Nitromalonaldehyde

Product 1

HCID 686948242-(4-Methylpiperazin-1-yl)-5-nitropyrimidineYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Nitro-malonaldehyde (1.57 g, 10 mmol) is dissolved in water (15 mL), followed by addition of 2-methyl-isothiourea (1.56 g, 5.6 mmol) and N-methylpiperazine (1.92 mL, 17.3 mL). After stirring at room temperature overnight, it is filtered and washed with water and hexane to yield 1.38 g (62%) of 2-(4-methyl-piperazin-1-yl)-5-nitro-pyrimidine as a white solid. MS (ESI) m/z 224.3 (M+H)+1. [Heterocycles. 1977, 6(12), 1999-2004].

Workup

  1. filtrationit is filtered
  2. washwashed with water and hexane

Sources & evidence

ORD record
ord-e8160db79e264ca28ffdb8bac3ab31b1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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