Methyl iodide → HCID 21948140, compound

HRID 1839401Notes

Reaction equation

HRID 1839401 reaction equation
[CH3:1][C:2]1(C)[CH2:7][CH2:6]CC(C)(C)N1.[Li][CH2:12]CCC.CN([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])C.N([C:31]1[N:32]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:33]2[C:38]([C:39](=[O:41])[CH:40]=1)=[C:37]([CH3:42])[CH:36]=[C:35]([O:43][CH2:44][CH3:45])[N:34]=2)C1C=CC=CC=1.CI.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:44]([O:43][C:35]1[N:34]=[C:33]2[C:38]([C:39](=[O:41])[C:40]([CH3:31])=[C:23]([N:21]([CH3:22])[C:20]3[CH:19]=[CH:6][CH:7]=[CH:2][CH:1]=3)[N:32]2[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[C:37]([CH2:42][CH3:12])[CH:36]=1)[CH3:45]

Participants

9

Reactant 6

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 130352,2,6,6-TetramethylpiperidineHCID 25517Ammonium ChlorideHCID 21948182HCID 21948182, compoundHCID 178418339Butyllithium

Product 1

HCID 21948140HCID 21948140, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-60 °C

Procedure

To a suspension of 2,2,6,6-tetramethylpiperidine (153 mg, 0.18 mL, 1.08 mmol) in THF (10 mL) at 0° C., was added n-BuLi via syringe (1.6 M, 0.68 mL, 1.08 mmol) and TMEDA. The reaction mixture was stirred for 1 h under argon. The reaction mixture was cooled to −60° C. using an acetone/dry ice bath and 2-anilino-7-ethoxy-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (100 mg, 0.269 mmol) was added via syringe as a solution in THF (5 mL). The mixture was stirred for 1 h. MeI was added via syringe and the reaction was allowed to warm to room temperature and stirred for 18 h. A saturated aqueous solution of NH4Cl (20 mL) and EtOAc (20 mL) was added, and the organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash chromatography using 7:3 to 100:0 EtOAc:Hex to give 3 products as follows:

Workup

  1. stirringThe mixture was stirred for 1 h
  2. temperatureto warm to room temperature
  3. stirringstirred for 18 h
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography
  8. customHex to give 3 products

Sources & evidence

ORD record
ord-7aad9a83a649412285930e2d12c22225
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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