Triethylamine → (R)-2-(prop-2-ynyl)-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

HRID 1432029Notes

Reaction equation

HRID 1432029 reaction equation
[N+:1]([C:4]1[C:9]([NH:10][C@H:11]([CH2:16][C:17]#[CH:18])[C:12](OC)=[O:13])=[CH:8][CH:7]=[CH:6][N:5]=1)([O-])=O.[NH4+].[Cl-].CCN(CC)CC>CO.[Fe]>[CH2:16]([C@@H:11]1[C:12](=[O:13])[NH:1][C:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:9]=2[NH:10]1)[C:17]#[CH:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 86604879(R)-methyl 2-(2-nitropyridin-3-ylamino)pent-4-ynoate

Product 1

HCID 86604880(R)-2-(prop-2-ynyl)-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A suspension of (R)-methyl 2-(2-nitropyridin-3-ylamino)pent-4-ynoate (220 mg, 0.883 mmol), iron (296 mg, 5.30 mmol) and NH4Cl in 10 mL of MeOH was heated to reflux for 4 h. After cooling to room temperature, 0.5 mL of NEt3 was added and the solution was stirred overnight. The solvent was evaporated and the residue was redissolved with EtOAc and filtered through a pad of silica gel. The filtrate was evaporated to dryness the title compound that was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was redissolved with EtOAc
  5. filtrationfiltered through a pad of silica gel
  6. customThe filtrate was evaporated to dryness the title compound that

Sources & evidence

ORD record
ord-28fc1f21fe1742f498e9319eafd45948
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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