Triethylamine → 7-chloro-2-methyl-1-(3-methylbutyl)-4-phenyl-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one

HRID 530131Notes

Reaction equation

HRID 530131 reaction equation
[Cl:1][C:2]1[N:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[CH:8]([CH3:15])[N:9]([CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[Cl:1][C:2]1[N:18]=[CH:17][C:5]2[N:6]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:7](=[O:16])[CH:8]([CH3:15])[N:9]([CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 895704037-chloro-2-methyl-1-(3-methylbutyl)-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one

Product 1

HCID 895704047-chloro-2-methyl-1-(3-methylbutyl)-4-phenyl-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-oneYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7-chloro-2-methyl-1-(3-methylbutyl)-1,4-dihydropyrido[3,4-b]pyrazin-3(2H)-one (103 mg, 0.38 mmol) in dichloromethane (7 mL) was added triethylamine (0.53 mL, 3.8 mmol), cupric acetate (140 mg, 0.77 mmol) and phenylboronic acid (94 mg, 0.77 mmol) followed by 4 Å molecular sieves (2.0 g). The reaction mixture was stirred for 30 h at rt with an air balloon. It was then filtered over celite to remove inorganic material, the organic phase was washed with aqueous sodium carbonate, dried with Na2SO4, and the solvent was removed under reduced pressure to give a crude residue, which was purified by silica gel flash column chromatography (eluent: 40% ethyl acetate in hexane) to give the desired product (Yield: 49%). 1HNMR (CDCl3, 300 MHz) δ 1.07-1.18 (m, 6H), 1.47 (d, J=6.6 Hz, 3H), 1.69-1.86 (m, 4H), 3.18-3.26 (m, 1H), 3.48-3.58 (m, 1H), 4.32 (q, J=6.9 Hz, 1H), 6.62 (s, 1H), 6.87-7.05 (m, 1H), 7.27-7.35 (m, 2H), 7.39 (s, 1H), 7.53-7.65 (m, 3H).

Workup

  1. filtrationIt was then filtered over celite
  2. customto remove inorganic material
  3. washthe organic phase was washed with aqueous sodium carbonate
  4. dry with materialdried with Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customto give a crude residue, which
  7. customwas purified by silica gel flash column chromatography (eluent: 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3ec9d4108b304cf8afa26d7bec1c1402
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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