Diethyl Ether → HCID 12074084, compound

HRID 1356990Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([CH:20]([OH:24])[CH2:21][CH2:22][CH3:23])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1.C([Mg]Cl)CC.C(OCC)C.CO.C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Part A: 8-(2,4-dichlorophenyl)-2-ethyl-3-(1-hydroxybutyl)imidazo[1,2-a]pyrazine: The aldehyde (1.6 g, 5.0 mmol, Part D of Example 1) was dissolved in anhydrous THF (25.0 mL) and cooled to −78° C. under nitrogen. To this mixture was added dropwise 2.0 M n-PrMgCl in diethyl ether (6.7 mL, 14.4 mmol) and stirred at −78° C. for 4 h. TLC (1:10 MeOH/CH2Cl2) revealed absence of starting material spot (Rf=0.88) and showed a new spot at Rf=0.05. The reaction mixture was quenched with saturated NH4Cl (30.0 mL), stirred the mixture for 10 min., extracted with EtOAc (3×100 mL), dried (MgSO4) and concentrated in vacuum to afford yellow oil. The residue was purified by flash column chromatography on a silica gel using 2.5% MeOH/CH2Cl2 to afford 1.63 g (84%, mp 159-160° C.) of desired product as white solid.

Workup

customThe reaction mixture was quenched with saturated NH4Cl (30.0 mL)
stirringstirred the mixture for 10 min.
extractionextracted with EtOAc (3×100 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuum
customto afford yellow oil
customThe residue was purified by flash column chromatography on a silica gel using 2.5% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-7acf3808dbd441c1884d99834af85f59
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589952B2

Reaction notes

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