1-(Ethanesulfonyl)piperazine → HCID 66744532, compound

HRID 1959339Notes

Reaction equation

HRID 1959339 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH3:12])[C:5]2=[O:13].[CH2:14]([S:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)(=[O:18])=[O:17])[CH3:15]>COCCO>[CH2:14]([S:16]([N:19]1[CH2:20][CH2:21][N:22]([C:2]2[N:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[N:8]=[CH:7][N:6]([CH3:12])[C:5]3=[O:13])[CH2:23][CH2:24]1)(=[O:18])=[O:17])[CH3:15]

Participants

4

Reactant 2

HCID 4152941-(Ethanesulfonyl)piperazineHCID 151481226-bromo-3-methyl-4(3H)-Pteridinone

Product 1

HCID 66744532HCID 66744532, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-bromo-3-methyl-pteridin-4-one (5.516 g, 22.88 mmol) in 2-methoxyethanol (50.81 mL) was treated with 1-ethylsulfonylpiperazine (6.118 g, 34.32 mmol) and the resulting suspension heated for 2 hours at 100° C. The reaction mixture was cooled in an ice-water bath and resultant precipitate collected and washed with cold methanol to give the product as a yellow solid (5.02 g, 65% Yield). 1H NMR (400.0 MHz, DMSO) d 1.25 (t, 3H), 3.10 (q, 2H), 3.34 (m, 4H), 3.49 (s, 3H), 3.85 (m, 4H), 8.37 (s, 1H), 8.84 (s, 1H) ppm; MS (ES+) 339

Workup

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. customresultant precipitate collected
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-29af5d435338488abc1ce488fa20662a
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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