p-Toluenesulfonic acid → 4-methyl-2-(methylthio)-6-(1H-pyrazol-4-ylamino)-5-pyrimidinecarbonitrile

HRID 390053노트

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HRID 390053 반응식
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.C1(S([N:22]2[CH:26]=[C:25]([NH2:27])[CH:24]=[N:23]2)(=O)=O)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:27][C:25]2[CH:26]=[N:22][NH:23][CH:24]=2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 582963084-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrileHCID 582963261-(phenylsulfonyl)-1H-pyrazol-4-amine

생성물 1

HCID 672232944-methyl-2-(methylthio)-6-(1H-pyrazol-4-ylamino)-5-pyrimidinecarbonitrile수율 45.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a solution of 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile (6.45 g, 32.2 mmol) and 1-(phenylsulfonyl)-1H-pyrazol-4-amine (7.2 g, 32.2 mmol) in 1,4-dioxane (150 mL) was added 4-methylbenzenesulfonic acid (3.06 g, 16.1 mmol). The reaction mixture was stirred overnight at 90° C. After cooling to room temperature, the precipitate was filtered, washed with saturated NaHCO3 solution and then water, dried and washed with petroleum and the mixture solvent (petroleum ether:ethyl acetate=4:1) successively to give 4-methyl-2-(methylthio)-6-(1H-pyrazol-4-ylamino)-5-pyrimidinecarbonitrile (intermediate 30, 3.6 g) as a pale solid. MS: M(C10H10N6S)=246.30, (M+1)+=247.1; 1HNMR (300 mHz, DMSO-d6) δ ppm 12.69 (1H, s), 9.87 (1H, s), 7.97 (1H, s), 3.33 (3H, m), 2.42 (3H, s). The organic eluents were concentrated under reduced pressure and the residue was treated with the same method above to afford 4-methyl-2-(methylthio)-6-{[1-(phenylsulfonyl)-1H-pyrazol-4-yl]amino}-5-pyrimidinecarbonitrile (intermediate 29, 4.26 g, 34.4% yield) as a yellow solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialwater, dried
  5. washwashed with petroleum

출처 및 근거

ORD 기록
ord-4d9cac57ee3d42fa829e969158e40b08
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383635B2

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