Acetic Acid → N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine

HRID 410407

반응식

HRID 410407 반응식
Cl[C:2]1[N:7]=[C:6]([CH:8]([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[NH2:15].CC(O)=O>O1CCOCC1.C(Cl)Cl>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:7]=[C:6]([CH:8]([F:10])[F:9])[CH:5]=[CH:4][N:3]=2)[CH:16]=[C:17]([CH3:19])[CH:18]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 30185263-Bromo-5-methylanilineHCID 717429242-Chloro-4-(difluoromethyl)pyrimidine

생성물 1

HCID 67249363N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine수율 72.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

The product of Step 1 (4.75 g, 23 mmol) and 3-bromo-5-methylaniline (5.59 g, 30 mmol) were diluted with dioxane (33 mL) to which AcOH (1.32 mL, 23 mmol) was added. The resulting mixture was heated to reflux and kept stirring for 30 h after which it was recooled to room temperature, diluted with CH2Cl2 and absorbed on silica prior to purification by flash chromatography to afford N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine (5.2 g, 16.6 mmol). 1H NMR (600 MHz, CDCl3) δ 8.58 (d, J=4.9, 1H), 7.75 (s, 1H), 7.32 (s, 1H), 7.21 (s, 1H), 7.06-6.92 (m, 2H), 6.50-6.27 (m, 1H), 2.30 (s, 3H).

후처리

  1. additionwas added
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux
  4. customwas recooled to room temperature
  5. customabsorbed on silica
  6. customto purification by flash chromatography

출처 및 근거

ORD 기록
ord-52b2c69a4d41400a9d697cf06bd5a81d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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