1-Methylpiperazine → HCID 24797604, compound

HRID 2360570Notes

Reaction equation

HRID 2360570 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CCO>[CH:9]1([C:4]2[CH:5]=[C:6]([N:18]3[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]3)[N:7]=[C:2]([NH2:1])[N:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 218463674-Chloro-6-cyclopentylpyrimidin-2-amine

Product 1

HCID 24797604HCID 24797604, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude 2-amino-4-chloro-6-cyclopentylpyrimidine (92 mg, 0.47 mmol), and N-methyl piperazine (0.15 mL, 1.4 mmol) in EtOH (2 mL) was heated at 70° C. for 2 h. The reaction was cooled to rt and concentrated and the crude residue chromatographed (2 M NH3 in MeOH/CH2Cl2) to yield an oil (81 mg, 66%). MS (ESI): mass calcd. for C14H23N5, 261.2; m/z found, 262.3 [M+H]+. 1H NMR (CDCl3): 5.85 (s, 1H), 4.78 (s, 2H), 3.59 (t, J=5.0, 4H), 2.81 (q, J=8.7, 1H), 2.44 (t, J=5.0, 4H), 2.32 (s, 3H), 2.04-1.89 (m, 2H), 1.82-1.59 (m, 6H).

Workup

  1. concentrationconcentrated
  2. customthe crude residue chromatographed (2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8aed3ac022ac47ab96fde8e2f1d17beb
Source dataset
uspto-grants-2014_04
Patent number
US08686142B2

Reaction notes

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