4,6-Dichloro-5-methylpyrimidine → 5-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole

HRID 1619440

Reaction equation

CC(C)([O-])C.[K+].[CH:7]([C:10]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[O:12][N:11]=1)([CH3:9])[CH3:8].[Cl:22][C:23]1[C:28]([CH3:29])=[C:27](Cl)[N:26]=[CH:25][N:24]=1>C1COCC1>[Cl:22][C:23]1[N:24]=[CH:25][N:26]=[C:27]([O:21][CH:18]2[CH2:17][CH2:16][N:15]([C:13]3[O:12][N:11]=[C:10]([CH:7]([CH3:9])[CH3:8])[N:14]=3)[CH2:20][CH2:19]2)[C:28]=1[CH3:29]

Participants

Conditions

Temperature: 30 °C

Procedure

Potassium tert-butoxide (478 mg, 0.00426 moles) was added to a solution of 1-(3-iso-propyl-1,2,4-oxadiazol-5-yl)piperidin-4-ol (0.9 gm, 0.00426 moles) and 4,6-dichloro-5-methylpyrimidine (690 mg, 0.00426 moles) in dry THF (30 ml) at 0° C. and the reaction mixture was stirred for 20 hours at 30° C. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 900 mg product as off white solid.

Workup

additionThe reaction mixture was poured into ice cold water
extractionextracted with ethyl acetate
extractionThe organic extract
washwas successively washed with water & brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-2596b292049147a481c0de98949b0136
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772302B2

Linked notes

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