8-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one → HCID 9924704, compound

HRID 1813913Notes

Reaction equation

HRID 1813913 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[C:16]2[NH:15][C:14](=O)[CH2:13][N:12]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[C:11]=2[N:10]=[C:9]([CH3:27])[CH:8]=1)[CH2:4][CH3:5])[CH3:2].CSC.B>C1COCC1>[CH2:1]([CH:3]([O:6][C:7]1[C:16]2[NH:15][CH2:14][CH2:13][N:12]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[C:11]=2[N:10]=[C:9]([CH3:27])[CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 101558468-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 9924704HCID 9924704, compoundYield 117.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (13 mg, 0.0354 mmol) and 2M borane dimethylsulfide complex (BH3.DMS) (0.044 ml, 0.0884 mmol) in 2 ml of dry THF was heated at reflux for 2 hours. The mixture was quenched with 0.2 ml of methanol and 0.2 ml of concentrated hydrochloric acid (HCl) and the resulting mixture was stirred at room temperature for 2 hours, and then concentrated to dryness. The residue was quenched with water, neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 14.7 mg of the title compound as a brown crystals. The crystals were purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 9 mg of the title compound as a colorless oil. 1H NMR (CDCl3) δ 6.93(s,2H), 6.02(s,1H), 4.18(m,1H), 3.62(m,2H), 3.44(m,2H), 2.31(s,3H), 2.12(s,9H), 1.71(m,4H), 0.98(t,6H)ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe mixture was quenched with 0.2 ml of methanol and 0.2 ml of concentrated hydrochloric acid (HCl)
  4. concentrationconcentrated to dryness
  5. customThe residue was quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-abf86d0ae1dd4f778dfdc3bbacf1702c
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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