1-Methylpiperazin-2-one → Methyl 2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxylate

HRID 1911428Notes

Reaction equation

HRID 1911428 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][C:3]1=[O:8].Cl[C:10]1[N:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][N:11]=1>ClCCl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:10]2[N:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][N:11]=2)[CH2:4][C:3]1=[O:8]

Participants

4

Reactant 2

HCID 43990421-Methylpiperazin-2-oneHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 66589656Methyl 2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methylpiperazin-2-one (198 mg, 1.74 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of methyl 2-chloropyrimidine-5-carboxylate (300 mg, 1.74 mmol) in dichloromethane (4.70 mL) at 25° C. The resulting solution was stirred at room temperature for 4 h under nitrogen. The reaction mixture was concentrated and dissolved in ethyl acetate (25 ml) and NaOH (50 ml, 1M aqueous solution). The organic layer was washed with ethyl acetate (25 ml). The organic layers were combined and washed with brine (50 ml), dried using MgSO4, filtered and evaporated to dryness to afford methyl 2-(4-methyl-3-oxopiperazin-1-yl)pyrimidine-5-carboxylate (246 mg, 57%) as a cream solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (25 ml)
  3. washThe organic layer was washed with ethyl acetate (25 ml)
  4. washwashed with brine (50 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-b79a149712014fc5890b4bc398b4170c
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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