Lithium Hexamethyldisilazide → HCID 9969235, compound

HRID 1612379Notes

Reaction equation

HRID 1612379 reaction equation
[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[NH:8][C:7]1=[O:26])[CH2:4][CH3:5])[CH3:2].[CH3:27][Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:1]([CH:3]([N:6]1[C:14]2[CH:13]=[C:12]([CH3:15])[N:11]=[C:10]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])[C:9]=2[N:8]([CH3:27])[C:7]1=[O:26])[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 10155052HCID 10155052, compound

Product 1

HCID 9969235HCID 9969235, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1-ethylpropyl)-6-methyl-4-(2,4,6-trimethylphenoxy)-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (100 mg, 0.28 mmol) in 5 ml of dry THF was treated with lithium bis(trimethylsilyl)amide (0.31 ml, 1 M in THF, 0.31 mmol) at −78° C. After 20 min, the mixture was quenched with 1 ml of methyl iodide and stirred at room temperature for 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 110 mg of an off-white solid which was recrystallized from isopropyl ether to give white crystals. Mp 152–154° C.; 1H NMR (CDCl3) δ 6.91 (s, 2H), 6.57 (s, 1H), 4.18 (m, 1H), 3.73 (s, 3H), 2.32 (s, 3H), 2.27 (s, 3H), 2.12 (s, 6H), 1.9–2.1 (m, 2H), 1.7–1.9 (m, 2H), 0.88 (t, 6H) ppm.

Workup

  1. customthe mixture was quenched with 1 ml of methyl iodide
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecfcb7c0f46b4e888ad605cea9e161c0
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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