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

HRID 1813912Notes

Reaction equation

HRID 1813912 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7]([NH:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])=[N:8][C:9]([CH3:18])=[CH:10][C:11]=1[O:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:14]([CH:13]([O:12][C:11]1[C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:19]([C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[C:7]=2[N:8]=[C:9]([CH3:18])[CH:10]=1)[CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 21912251HCID 21912251, compound

Product 1

HCID 101558468-(1-ethyl-propoxy)-6-methyl-4-(2,4,6-trimethyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 104.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution of 2-chloro-N-[4-(1-ethyl-propoxy)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-pyridin-3-yl]-acetamide (40 mg, 0.099 mmol) in dry THF was added 1.0 M lithium bistrimethylsilyl amide (LiN(SiMe3)2) in THF (0.3 ml, 0.3 mmol) at −78° C. and stirred at that temperature for 1 hour, then warmed to room temperature for 30 min. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 38 mg of the title compound as a tan crystals. The crystals were purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give 29 mg (81%) of the title compound as a white crystal, mp 179-181° C. 1H NMR (CDCl3) δ 7.75(s,1H), 6.95(s,2H), 6.09(s,1H), 4.22(s,2H), 4.22(m,1H), 2.32(s,3H), 2.17(s,3H), 2.16(s,6H), 1.71(m,4H), 0.97(m,6H)ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5aa4be5f1853498cb56376c6774fa3b8
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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