Dimethyl Sulfoxide → 4-(6-Methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butanal

HRID 1847039Notes

Reaction equation

HRID 1847039 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:21](=[O:22])[CH:20]=[N:19][C:18]2[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[N:26][C:17]1=2.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][C:18]2[N:19]=[CH:20][C:21](=[O:22])[N:16]([CH2:15][CH2:14][CH2:13][CH:12]=[O:11])[C:17]=2[N:26]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 867249634-(4-Hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 867249644-(6-Methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butanalYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (0.155 ml, 1.81 mmol) in dichloromethane (1.5 ml) was cooled to −78° C., a solution of dimethyl sulfoxide (0.128 ml, 1.81 mmol) in dichloromethane (1.5 ml) was added dropwise under a stream of argon and the solution was stirred at the same temperature for 15 minutes. A solution of 4-(4-hydroxybutyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (150 mg, 0.60 mmol) in dichloromethane (1.5 ml) was added dropwise to the reaction solution and the mixture was further stirred at the same temperature for 1.5 hours. Triethylamine (0.503 ml, 3.61 mmol) was added to the reaction solution, the temperature was raised to room temperature and a saturated ammonium chloride solution and dichloromethane were added. The organic layer was separated, washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to yield 148 mg (100%) of the title compound in the form of a yellow solid. The product was used as such for the next step without purification.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 1.5 hours
  2. customThe organic layer was separated
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-203394475c7c4405a61e9c05d7117642
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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