Potassium Carbonate → 5-Bromo-1-methyl-3-(3-methylisothiazol-5-ylamino)pyrazin-2(1H)-one

HRID 1022243

반응식

HRID 1022243 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[S:4][N:3]=1.Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=[C:13]([Br:15])[N:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[Br:15][C:13]1[N:14]=[C:9]([NH:7][C:5]2[S:4][N:3]=[C:2]([CH3:1])[CH:6]=2)[C:10](=[O:17])[N:11]([CH3:16])[CH:12]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 323073-Methylisothiazol-5-amineHCID 634876Binap, (A+-)-HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

생성물 1

HCID 866846005-Bromo-1-methyl-3-(3-methylisothiazol-5-ylamino)pyrazin-2(1H)-one수율 50%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

A sealed tube equipped with a magnetic stirrer was charged with 3-methylisothiazol-5-amine (170 mg, 1.5 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (400 mg, 1.5 mmol), Pd(OAc)2 (84 mg, 0.375 mmol), BINAP (116 mg, 0.188 mmol), K2CO3 (450 mg, 4.5 mmol), and 1,4-dioxane (4 mL). After three cycles of vacuum/nitrogen flush, the mixture was heated at 120° C. in a sealed tube for 18 h. It was then cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (100:1 to 25:1) to afford 331a (220 mg, 50%) as a yellow solid. MS-ESI: [M+H]+ 301.0.

후처리

  1. customA sealed tube equipped with a magnetic stirrer
  2. customAfter three cycles of vacuum/nitrogen flush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography
  7. washeluting with dichloromethane/methanol (100:1 to 25:1)

출처 및 근거

ORD 기록
ord-c2387c97806f4e66aa95dbbbb8347ac1
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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