Triphenyl phosphite → Methyl 4-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate

HRID 716269

Reaction equation

HRID 716269 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH3:19])[C:6]1[C:15]([N+:16]([O-])=O)=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH3:19][N:5]1[CH2:4][C:3](=[O:2])[NH:16][C:15]2[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[N:7][C:6]1=2

Participants

7

Reactant 3

HCID 7540Triphenyl phosphiteHCID 58324470Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 58324455Methyl 4-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylateYield 68.8%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 516859Ammonium metavanadateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinate (2.7 g, 9.53 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (30.0 mg, 0.256 mmol), triphenyl phosphite (aprox 30 ul, 0.097 mmol), and Pt/C (300 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (110 psi) and stirred at room temperature for 16 h. The reaction was then depressurized and diluted with dichloromethane (100 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×20 mL). The filtrate was concentrated in vacuo to yield the title compound (1.45 g, 68%) as a white solid. [M+H] calc'd for C10H11N3O3, 222. found, 222.

Workup

  1. temperaturewas then refluxed for 30 min
  2. filtrationThe hot solution was filtered through a pad of celite
  3. washwashed with hot dichloromethane (3×20 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fe21c1d1f92845fea14941378afd5ec2
Source dataset
uspto-grants-2015_11
Patent number
US09187497B2

Linked notes

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