Piperazine → 2-Methoxymethyl-4-piperazin-1-yl-pyrimidine

HRID 2227843Notes

Reaction equation

HRID 2227843 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8](CS([O-])(=O)=O)[CH:7]=[CH:6][N:5]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O1CCCC1>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 865918782-Methoxymethyl-pyrimidin-4-yl-methanesulfonate

Product 1

HCID 109547722-Methoxymethyl-4-piperazin-1-yl-pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxymethyl-pyrimidin-4-yl-methanesulfonate (prepared according to the method of Preparation One, Step A, 43.6 g, 200 mmol) in tetrahydrofuran (400 mL) was added piperazine (34.4 g, 400 mmol). This mixture was heated to reflux for 0.5 h, cooled to room temperature, and filtered. The filtrate was concentrated and dried under reduced pressure to give the title compound as a semi-solid, 36.6 g (85%). 1H NMR (CDCl3, 300 MHz) δ2.45 (br s, 1H), 2.88 (m, 4H), 3.45 (s, 3H), 3.72 (m, 4H), 4.46 (s, 2H), 6.38 (d, 1H), 8.22 (d, 1H); MS (TS) 209 (MH+).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 0.5 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-492ccb319bfc43e682b2b00e71261977
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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