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

HRID 586197Notes

Reaction equation

HRID 586197 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) δ 2.45 (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-397753a5fa6943c3a178c4cc90ea9061
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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