Triethylamine → 2,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

HRID 706339Notes

Reaction equation

HRID 706339 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:23]=[CH:22][CH:21]=[N:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[H][H].CCN(CC)CC>CCO.C1COCC1.[Pd]>[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 45725312,3-Bis(4-methylphenyl)pyrido[2,3-b]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 666645252,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 2,3-dip-tolylpyrido[2,3-b]pyrazine (step 1) (181 g, 487 mmol) in EtOH/THF (1:2, 2100 ml) was treated with 10% palladium on carbon (30 g, 28.8 mmol) and the reaction mixture was placed under 0.1 bar of hydrogen at RT. After 2 days and 4 days respectively, additional batches of 10% palladium on carbon (10 g, 9.6 mmol, twice) were added along with Et3N (85 ml, 706 mmol, twice). After 7 days in total, the reaction mixture was filtered through Hyflo (filter material) and washed through with THF (2.5 L in portions). The filtrate was concentrated in vacuo to give a green/yellow solid. The solid was triturated with 1:1 TBME/heptane (500 ml) and filtered. The solid was washed with 1:1 TBME/heptane (200 ml) to give a pale yellow solid which was dried overnight to afford the title compound; HPLC (Agilent 1200), Rt 4.73 min, Method B.

Workup

  1. filtrationAfter 7 days in total, the reaction mixture was filtered through Hyflo (filter material)
  2. washwashed through with THF (2.5 L in portions)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a green/yellow solid
  5. customThe solid was triturated with 1:1 TBME/heptane (500 ml)
  6. filtrationfiltered
  7. washThe solid was washed with 1:1 TBME/heptane (200 ml)
  8. customto give a pale yellow solid which
  9. customwas dried overnight

Sources & evidence

ORD record
ord-6e98e232e0514a26943d31416cbb9468
Source dataset
uspto-grants-2015_11
Patent number
US09174985B2

Reaction notes

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