2-Chloro-6-(1-piperazinyl)pyrazine → 2-(3-Thienylmethoxy)-6-(1-Piperazinyl)Pyrazine

HRID 1357639Notes

Reaction equation

HRID 1357639 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][OH:7])=[CH:2]1.Cl[C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:12]=[N:11][CH:10]=1>>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[N:14]=2)=[CH:2]1

Participants

3

Reactant 2

HCID 1079922-Chloro-6-(1-piperazinyl)pyrazineHCID 123570Thiophene-3-methanol

Product 1

HCID 98786962-(3-Thienylmethoxy)-6-(1-Piperazinyl)PyrazineYield 64.7%

Conditions

Temperature
105 °C

Procedure

The title compound was prepared according to the procedure of Example 20 starting from 3-thiophenemethanol (6.05 g, 53.0 mmol), K-t-BuO (0.897 g, 7.99 mmol) and 6-chloro-2-(1-piperazinyl)pyrazine (0.845 g, 4.25 mmol: obtained in Example 13, step 2). The reaction mixture was stirred at 105° C. for 7.5 h. Following chromatography on silica, solvents were evaporated off. The remaining oil was redissolved in ethyl acetetate and filtered through a short plug of alumina (5×3 cm) using ether/MeOH (96:4) as eluent. Solvent removal in vacuo gave 0.76 g (64%) of the title compound as a colorless oil. HRMS m/z for C13H16N4OS (M)+ calcd for 276.1045, found 276.1037. Anal. (C13H16N4OS.0.25 H2O) C, H, N.

Workup

  1. customThe title compound was prepared
  2. customwere evaporated off
  3. dissolutionThe remaining oil was redissolved in ethyl acetetate
  4. filtrationfiltered through a short plug of alumina (5×3 cm)
  5. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-7730a9549cde4884b596193f78a1239e
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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