Methyl iodide → HCID 57932912, compound

HRID 1432710Notes

Reaction equation

HRID 1432710 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[N:8]([CH3:12])[N:9]=[CH:10][N:11]=2)[S:4][C:3]=1[C:13]1[N:17]2[N:18]=[C:19]([CH3:27])[CH:20]=[C:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:16]2=[N:15][C:14]=1[CH3:28].[CH2:29]1COCC1.[Li]C(C)(C)C.CI>CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:29])[N:11]=2)[S:4][C:3]=1[C:13]1[N:17]2[N:18]=[C:19]([CH3:27])[CH:20]=[C:21]([CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[C:16]2=[N:15][C:14]=1[CH3:28]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 579330443-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418306HCID 178418306, compound

Product 1

HCID 57932912HCID 57932912, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a −78° C. solution of 3-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.72 mmol) and THF (5 mL) is added 1.7 M tert-BuLi (0.47 mL, 0.80 mmol). After 15 minutes MeI (0.052 mL, 0.83 mmol) is added and the solution warmed to ambient temperature. The solution is diluted with EtOAc (40 mL), washed with brine (40 mL), dried over MgSO4, filtered and concentrated. The solution is recrystallized from acetone:hexane furnish the title compound (0.13 g, 0.30 mmol, 42%). 1H NMR (CDCl3) δ0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.36 (s, 3H), 2.51 (s, 6H), 3.27-3.39 (m, 1H), 3.40 (s, 3H), 6.72 (s, 1H), 8.02 (s, 1H). LC/MS (m/z): calcd. for C21H25ClN6S (M+H)+: 429.2; found: 429.2.

Workup

  1. washwashed with brine (40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solution is recrystallized from acetone

Sources & evidence

ORD record
ord-e56c3478e7164bd39403f1f0681c260c
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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