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

HRID 1092125Notes

Reaction equation

HRID 1092125 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-c33c1b2de7674f1f99e23a7122758019
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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