Potassium Carbonate → 4-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methylsulfanyl-pyridin-3-ylamino)pyrimidine-5-carbonitrile

HRID 2067139Notes

Reaction equation

HRID 2067139 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]2[CH:12]=[N:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH:26]([C:29]1[N:33]=[C:32]([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[O:31][N:30]=1)([CH3:28])[CH3:27].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH:26]([C:29]1[N:33]=[C:32]([CH:34]2[CH2:39][CH2:38][N:37]([C:2]3[C:7]([C:8]#[N:9])=[C:6]([NH:10][C:11]4[CH:12]=[N:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=4)[N:5]=[CH:4][N:3]=3)[CH2:36][CH2:35]2)[O:31][N:30]=1)([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 534008274-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidine hydrochlorideHCID 859846374-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile

Product 1

HCID 582164034-[4-(3-Isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-6-(6-methylsulfanyl-pyridin-3-ylamino)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-6-(6-methylsulfanyl-pyridin-3-ylamino)-pyrimidine-5-carbonitrile (80.00 mg, 0.29 mmol) in DMF (2 ml) was mixture with Potassium Carbonate (79.62 mg, 0.58 mmol), added 4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidine hydrochloride (237.4 mg, 1.08 or 1.02 mmol) in DMF (1 ml) and left stirring at room temperature for 1 hour. Reaction was worked up with ethyl acetate, sodium bicarbonate, dried with magnesium sulfate, filtered and concentrate under high vacuum. Compound was recrystallized using hexane in ethyl acetate to afford Compound B136. 1H NMR 400 MHz DMSO δ (ppm): 9.48 (s, 1H), 8.55 (d, 1H), 8.35 (s, 1H), 8.19 (s, 1H), 7.77 (d, 1H), 7.26 (d, 1H), 4.52 (m, 2H), 3.48 (m, 1H), 3.37 (m, 2H), 3.32 (s, 3H), 3.04 (m, 1H), 2.14 (m, 2H), 1.75 (m, 2H), 1.33 (d, 6H).

Workup

  1. waitleft
  2. customReaction
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate under high vacuum
  6. customCompound was recrystallized
  7. customto afford Compound B136

Sources & evidence

ORD record
ord-18828e7cc0f24b13a7ceca03ecf3625f
Source dataset
uspto-grants-2012_10
Patent number
US08293751B2

Reaction notes

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