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

HRID 410407

反応式

HRID 410407 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-52b2c69a4d41400a9d697cf06bd5a81d
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

関連ノート

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