Sodium Bicarbonate → 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehyde

HRID 551869

Reaction equation

HRID 551869 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.CC1(C)N([O])C(C)(C)CCC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724126TempoHCID 587289965-Bromo-3-(4-hydroxymethyl-phenylamino)-1-methyl-1H-pyrazin-2-one

Product 1

HCID 587289094-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound (2) (3.1 g; 10 mmol) was dissolved in 150 mL CH2Cl2 at rt under N2. Solid 12 (5.1 g; 20 mmol) was added portion-wise to the stirring reaction, followed by catalytic 2,2,6,6-tetramethyl-1-piperdinyloxy, free radical (TEMPO; 0.23 g; 1.50 mmol). Saturated sodium bicarbonate solution was then added (20 mL) and the reaction allowed to stir overnight at rt under N2. The resulting light orange solid was filtered off and washed repeatedly with CH2Cl2 and diethyl ether until the extractions ran clear and colorless. After drying, 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehyde (3) was obtained in nearly quantitative yields (3.1 g) and was carried directly on to the next reaction. MS 308.01 & 310.01 (M+H)

Workup

  1. customto the stirring reaction
  2. filtrationThe resulting light orange solid was filtered off
  3. washwashed repeatedly with CH2Cl2 and diethyl ether until the extractions
  4. customAfter drying

Sources & evidence

ORD record
ord-d7d45fec2b7b410bb267653d07ccdd85
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Linked notes

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