Hexane → HCID 57932938, compound

HRID 1432673Notes

Reaction equation

HRID 1432673 reaction equation
Br[C:2]1[S:3][C:4]([C:8]2[N:12]3[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]3=[N:10][C:9]=2[CH3:23])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.CCCCCC.[O:35]1[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]1>C1COCC1.CCOC(C)=O>[O:35]1[CH2:36][CH:37]=[C:38]([C:2]2[S:3][C:4]([C:8]3[N:12]4[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]4=[N:10][C:9]=3[CH3:23])=[C:5]([CH3:7])[N:6]=2)[CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 68840065HCID 68840065, compoundHCID 178418339Butyllithium

Product 1

HCID 57932938HCID 57932938, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

370 mg of 3-(2-Bromo-4-methyl-thiazol-5-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.93 mmol) is dissolved in 10 ml of dry THF and cooled to −78° C. 0.6 ml of n-BuLi 2.0 M in hexane (1.2 mmol) is added and stirred at −78° C. for 30 min. 141 mg of tetrahydro-4H-pyran-4-one (1.41 mmol) is added and stirred at −78° C. for 2 h. The reaction mixture is diluted with AcOEt, washed with sat. NH4Cl, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=10:3:1) to give 152 mg of the title compound. Yield 40%: mass spectrum (m/e): 415 (M+1). 1H NMR (CDCl3): δ 6.74 (s, 1H), 3.99 (t, J=2.2 Hz, 4H), 3.97 (t, J=2.2 Hz, 4H), 3.35 (m, 1H), 3.20 (s, OH), 2.56 (s, 3H), 2.48 (s, 3H), 2.36 (s, 3H), 1.88 (m, 4H), 0.91 (t, J=7.3 Hz, 6H).

Workup

  1. stirringstirred at −78° C. for 2 h
  2. washwashed with sat. NH4Cl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-daf7ec1815ae4c82811f5f8d73477bc3
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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