Diethyl Ether → HCID 178426231, compound

HRID 537900Notes

Reaction equation

HRID 537900 reaction equation
C[Li].CCOCC.[CH3:8][C:9]1[N:14]2[CH:15]=[C:16]([CH2:18][S:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:24]=3)[N:17]=[C:13]2[N:12]=[C:11]([CH3:31])[CH:10]=1.Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CS(C)=O.O>[CH3:8][C:9]1[N:14]2[CH:15]=[C:16]([CH:18]([S:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:24]=3)[CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:17]=[C:13]2[N:12]=[C:11]([CH3:31])[CH:10]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 767274-(2-Chloroethyl)morpholineHCID 178418348HCID 178418348, compoundHCID 178426237HCID 178426237, compound

Product 1

HCID 178426231HCID 178426231, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of methyl lithium in ether (1.60 M, 0.205 mL, 0.328 mmol) was added dropwise to dimethyl sulfoxide (2.00 mL, 28.2 mmol) and the mixture left to stir for 40 minutes at room temperature. A solution of 5,7-Dimethyl-2-(4-phenyl-1H-imidazol-2-ylsulfanylmethyl)-imidazo[1,2-a]pyrimidine (0.100 g, 0.298 mmol) and N-(2-chloroethyl)morpholine (0.0666 g, 0.358 mmol) in dimethyl sulfoxide was added dropwise to the generated dimsyl anion. The resulting mixture was stirred at 80° C. for 45 minutes. After cooling to room temperature, water was carefully added and the mixture was extracted with ethyl acetate (20 mL). The combined organic extracts were dried over sodium sulfate and the solvent removed in vacuo. Column chromatography of the crude product using ethyl acetate:methanol (95:5 v/v) gave the product as a yellow oil. It was dissolved in a minimum amount of methanol and ethereal hydrogen chloride was added dropwise to precipitate the hydrochloride salt of title compound as a yellow solid which was collected by filtration and washed with ether (71 mg, 49%). LC-MS: m/z=449.3 (MH+), tR=0.37 min, method C.

Workup

  1. waitthe mixture left
  2. stirringThe resulting mixture was stirred at 80° C. for 45 minutes
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate (20 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4ab285c534b941399ca2bd891d6577a9
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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