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

HRID 2377925Notes

Reaction equation

HRID 2377925 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[O:6][N:5]=1)([CH3:3])[CH3:2].[Cl:16][C:17]1[C:22]([CH3:23])=[C:21](Cl)[N:20]=[CH:19][N:18]=1>C1COCC1.CC(C)([O-])C.[K+]>[Cl:16][C:17]1[C:22]([CH3:23])=[C:21]([O:15][CH:12]2[CH2:11][CH2:10][N:9]([C:7]3[O:6][N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=3)[CH2:14][CH2:13]2)[N:20]=[CH:19][N:18]=1

Participants

5

Reactant 2

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Product 1

HCID 865973665-(4-(6-Chloro-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazoleYield 72.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 23665647Potassium tert-butoxideSolvent

Procedure

To a solution of 1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-ol (3.65 g, 17 mmol) and 4,6-dichloro-5-methylpyrimidine (2.83 g, 17 mmol) in THF (70 mL), 1M potassium-t-butoxide in THF (16 mL, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 10 min. The crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v) to provide 4-chloro-6-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yloxy]-5-methyl-pyrimidine as a solid (4.15 g, 71%). Exact mass calculated for C15H20ClN5O2337.13, found 338.2 (MH+).

Workup

  1. customThe crude mixture was purified by column chromatography on silica gel with hexane/ethyl acetate (3:1 v/v)

Sources & evidence

ORD record
ord-f70cbb9f18744ce5affeeafd94314f23
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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