1-Methylpiperazine → Methyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

HRID 1399596Notes

Reaction equation

HRID 1399596 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]1[N:14]=[C:13]([CH3:15])[C:12]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:10]=1>O1CCCC1>[CH3:15][C:13]1[C:12]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19][CH3:20])=[O:18])=[C:11]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[N:10]=[C:9]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[N:14]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 50996969Methyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate was prepared according to the general method A starting from 1-methylpiperazine (0.132 mL; 1.18 mmol) and methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.098 g; 0.235 mmol) in tetrahydrofuran (2 mL). Purification by flash-chromatography on silica gel using a gradient of methanol (0-6%) in dichloromethane furnished 68 mg (74%) of the title compound as an oil. ESI/APCI(+): 397 (M+H)a). ESI/APCI(−): 395 (M−H).

Workup

  1. customMethyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of methanol (0-6%) in dichloromethane

Sources & evidence

ORD record
ord-6b52b8d67bfb4cad921de2be16884a85
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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