m-Chloroperbenzoic acid → N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

HRID 859973Notes

Reaction equation

HRID 859973 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N:15][N:16]4[C:21]([S:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-:29].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N:15][N:16]4[C:21]([S:22]([CH3:23])=[O:29])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10339828N-cyclopentyl-4-[2-isobutyl-7-(methylthio)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine

Product 1

HCID 10453435N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of N-cyclopentyl-4-[2-isobutyl-7-(methylthio)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (700 mg, 1.83 mmol) in dichloromethane (30 mL) was added sodium bicarbonate solid (500 mg), and m-chloroperbenzoic acid (451 mg, ˜70% pure, 1.83 mmol). The mixture was stirred at 0° C. for 20 minutes and then quenched by the addition of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate. The biphasic mixture was allowed to warm to room temperature and stirred vigorously for 15 minutes. The layers were separated and the organic layer washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration in vacuo provided N-cyclopentyl-4-[2-isobutyl-7-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine (720 mg, 99%) as a yellow solid. 1H NMR (CDCl3) δ 8.38–8.29 (m, 2H), 7.51–7.44 (m, 2H), 6.77 (d, 1H), 5.24 (m, 1H), 4.38 (m, 1H), 3.13 (s, 3H), 3.08–2.91 (m, 2H), 2.25–2.05 (m, 3H), 1.82–1.54 (m, 6H), 0.98 (m, 6H); MS m/z 398 (M+1).

Workup

  1. customquenched by the addition of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate
  2. temperatureto warm to room temperature
  3. stirringstirred vigorously for 15 minutes
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. extractionThe aqueous layer was extracted with dichloromethane
  7. dry with materialthe combined organics were dried over sodium sulfate
  8. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-83b42719fcf7437dad1db953d08e92d7
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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