1-Methylpiperazine → HCID 58638525, compound

HRID 646925Notes

Reaction equation

HRID 646925 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN(C=O)C>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]3)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][N:3]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 58638538HCID 58638538, compound

Product 1

HCID 58638525HCID 58638525, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-4-(4-methyl-piperidin-1-yl)-5-nitro-pyrimidine (as prepared in the previous step) (257 mg, 1.00 mmol) in DMF (10 mL) was added 1-methyl piperazine (110 μL, 1.00 mmol). The resulting mixture was heated at 80° C. for 48 h. The reaction mixture was allowed to cool to room temperature and partitioned between water/EtOAc. The EtOAc layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (0-10% MeOH:EtOAc) to obtain the title compound (192 mg, 63%). 1H-NMR (CDCl3; 400 MHz): δ 8.76 (s, 1H), 3.90 (br m, 6H), 2.96 (m, 2H), 2.40 (m, 4H), 2.32 (s, 3H), 1.82-1.6 (m, 3H), 1.2-1.3 (m, 2H), 1.02 (d, 3H, J=6.5 Hz).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water/EtOAc
  3. customThe EtOAc layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified on silica (0-10% MeOH:EtOAc)

Sources & evidence

ORD record
ord-36c6ff3b46a84b399cf9a5f6302e46a9
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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