Potassium Carbonate → 4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-2-methyl-pyrimidine-5-carbonitrile

HRID 2067132Notes

Reaction equation

HRID 2067132 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[N:5]=[C:4]([CH3:21])[N:3]=1.[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH:22]([C:25]1[N:29]=[C:28]([CH:30]2[CH2:35][CH2:34][N:33]([C:2]3[C:7]([C:8]#[N:9])=[C:6]([O:10][C:11]4[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=4)[N:5]=[C:4]([CH3:21])[N:3]=3)[CH2:32][CH2:31]2)[O:27][N:26]=1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 242088454-(3-(Propan-2-yl)-1,2,4-oxadiazol-5-yl)piperidineHCID 866079814-Chloro-6-(4-methanesulfonyl-phenoxy)-2-methyl-pyrimidine-5-carbonitrile

Product 1

HCID 103229864-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(4-methanesulfonyl-phenoxy)-2-methyl-pyrimidine-5-carbonitrileYield 25.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-6-(4-methanesulfonyl-phenoxy)-2-methyl-pyrimidine-5-carbonitrile (80.0 mg, 0.25 mmol) and 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine (107.1 mg, 0.50 mmol) in DMF (1 mL) was added potassium carbonate (68.3 mg, 0.50 mmol) and the resulting mixture was left stirring for 2 hours at room temperature. Worked up with ethyl acetate, sodium bicarbonate, dried with magnesium sulfate and evaporated. The crude product was crystallized with ethyl acetate/hexane-over night and filtered off to afford Compound A164 as a yellow solid (30.6 mg). LCMS (ESI) for C23H26N6O4S: m/z 483.3 (M+H+, 100%), 1H NMR 400 MHz CDCl3 δ (ppm): 8.00 (d, 2H), 7.38 (d, 2H), 4.82 (m, 2H), 3.45 (m, 2H), 3.31 (m, 1H), 3.10 (s, 3H), 3.08 (m, 1H), 2.35 (s, 3H), 2.24 (m, 2H), 2.03 (m, 2H), 1.34 (d, 6H).

Workup

  1. waitthe resulting mixture was left
  2. dry with materialdried with magnesium sulfate
  3. customevaporated
  4. customThe crude product was crystallized with ethyl acetate/hexane-over night
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-2a3cfb11658e4363a0b2f15c4f7e0b1e
Source dataset
uspto-grants-2012_10
Patent number
US08293751B2

Reaction notes

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