Tetrahydrofuran → 2-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine-5-carbaldehyde

HRID 2242216Notes

Reaction equation

C([Li])CCC.Cl[C:7]1[CH:8]=[N:9][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[N:11][CH:12]=1.C1C[O:31][CH2:30]C1>CN(C=O)C>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[N:9]=[CH:8][C:7]([CH:30]=[O:31])=[CH:12][N:11]=3)[N:17]=2)=[CH:19][CH:20]=1)[CH:25]([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (4.77 mL, 7.16 mmol) was added to a solution of 5-chloro-2-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine (1.5 g, 4.77 mmol) and THF (50 mL) at −78° C. and stirred for 7 hours DMF (3 mL) was added to the reaction mixture, warmed to 0° C. and stirred for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (25 mL) and the organic layer was separated and washed with water (3×25 mL) and brine (1×25 mL) and concentrated in vacuo to provide the title compound (1.13 g, 76% yield) as an orange solid.

Workup

additionwas added to the reaction mixture
customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL)
stirringstirred at room temperature for 12 hours
additionThe reaction mixture was diluted with EtOAc (25 mL)
customthe organic layer was separated
washwashed with water (3×25 mL) and brine (1×25 mL)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-de8ab14b3d924962abfc769dbb8f72f4
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671043B2

Reaction notes

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