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

HRID 716298Notes

Reaction equation

HRID 716298 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH:20]([CH3:22])[CH3:21])[C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)C.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH:20]([N:6]1[CH2:5][C:4](=[O:3])[NH:17][C:16]2[CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[N:8][C:7]1=2)([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 7540Triphenyl phosphiteHCID 58324358Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 58324447Methyl 4-isopropyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylateYield 93%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 516859Ammonium metavanadateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinate (2.39 g, 7.35 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (15.0 mg, 1.13 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (240 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 (80 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 to yield the title compound (1.70 g, 93%) as a white solid. [M+H] calc'd for C12H15N3O3, 250. found, 250.

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

Sources & evidence

ORD record
ord-51e9205ecda1444e83bfc2bce8020ae7
Source dataset
uspto-grants-2015_11
Patent number
US09187497B2

Reaction notes

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