Tetrahydrofuran → HCID 10249287, compound

HRID 1813914Notes

Reaction equation

HRID 1813914 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[C:16]2[NH:15][C:14](=[O:17])[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].[CH2:28]1COCC1>>[CH2:1]([CH:3]([O:6][C:7]1[C:16]2[N:15]([CH3:28])[C:14](=[O:17])[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

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 101558468-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Product 1

HCID 10249287HCID 10249287, compound

Procedure

To a −78° C. solution of 8-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (50 mg, 0.136 mmol) in 3 ml of dry THF was added 1.0M of LiN[Si(CH3)3]2 in THF (0.14 ml, 0.14 mmol) at −78° C. After stirring at that temperature for 20 min, the reaction mixture was warmed to room temperature and stirred at room temperature overnight. The mixture was quenched with water and saturated ammonium chloride and extracted with ethyl acetate. The organic extract was washed with brine, dried and concentrated to give 51 mg of a golden oil. The oil was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 41 mg (79%) of the title compound as a golden oil. 1H NMR (CDCl3) δ 6.9(s,2H), 6.17(s,1H), 4.30(m,1H), 4.01(s,2H), 3.47(s,3H), 2.30(s,3H), 2.20(s,3H), 2.01(s,6H), 1.70(m,4H), 0.97(t,6H)ppm.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe mixture was quenched with water and saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8f0db46d18ec47bc926086227b01fc52
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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