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

HRID 431682Notes

Reaction equation

HRID 431682 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-ff68ebabbec6452ea6ef6727e50718a8
Source dataset
uspto-grants-2003_12
Patent number
US06660740B1

Reaction notes

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