Acetic Acid → 2-(4-Methylpiperazin-1-yl)pyrimidin-5-amine

HRID 2236415Notes

Reaction equation

HRID 2236415 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.C(O)(=O)C>CO.[Fe]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:14])=[CH:12][N:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 686948242-(4-Methylpiperazin-1-yl)-5-nitropyrimidine

Product 1

HCID 568284122-(4-Methylpiperazin-1-yl)pyrimidin-5-amineYield 78.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(4-methyl-piperazin-1-yl)-5-nitro-pyrimidine (446 mg, 2 mmol), iron powder (432 mg, 7.6 mmol), acetic acid (0.884 mL, 14 mmol) in methanol (8 mL) is heated at 65 C for 2 h. It is worked up as before to yield 302 mg (78%) of the title compound. MS (ESI) m/z 194 (M+H)+1.

Workup

  1. temperatureis heated at 65 C for 2 h

Sources & evidence

ORD record
ord-0cc379c496e449888e8d2cc4d44eb56d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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