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

HRID 984920Notes

Reaction equation

HRID 984920 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-pyrimidin4-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-d061c2d746f8492985808ea2a557bad2
Source dataset
uspto-grants-2005_03
Patent number
US06869943B2

Reaction notes

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