Water → HCID 178441138、化合物

HRID 253706ノート

反応式

HRID 253706 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[N:3]=1.[NH:22]1[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:25]2[C:24]([NH2:31])=[N:23]1.O.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[C:8]([C:6]1[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[N:3]=[C:2]([NH:31][C:24]2[C:25]3[C:26](=[N:27][CH:28]=[CH:29][CH:30]=3)[NH:22][N:23]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 179793884-Chloro-6-tert-butyl-2-(2-trifluoromethylphenyl)-pyrimidineHCID 178509226HCID 178509226、化合物

生成物 1

HCID 178441138HCID 178441138、化合物収率 5.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
165 °C

実験手順

A mixture of 4-chloro-6-tert-butyl-2-(2-trifluoromethyl-phenyl)-pyrimidine (0.10 g, 0.32 mmol) and 1H-pyrazolo[3,4-b]pyridin-3-ylamine (0.064 g, 0.48 mmol) was heated neat at 160-170° C. for 16 hours. The resulting residue was cooled, dissolved in N-methyl-pyrrolidinone (2 mL), then poured into water (20 mL) and sodium bicarbonate (5 mL) and extracted twice with ethyl acetate. The combined organic layers were washed four times with water, once with brine, then dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC to provide the title compound (0.007 g, 4% yield) as a yellow solid. 1H-NMR (500 MHz, DMSO-d6) δ 13.2 (br s, 1H), 10.6 (br s, 1H), 8.49 (m, 2H), 7.84 (d, J=7.8 Hz, 2H), 7.76 (m, 2H), 7.68 (m, 1H), 7.12 (m, 1H), 1.32 (s, 9H) ppm; LC-MS 413.08 (M+H); Rt (Method A) 3.112 minutes.

後処理

  1. temperatureThe resulting residue was cooled
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed four times with water
  4. dry with materialonce with brine, then dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-2d0dece3dd644c4b954241da15b1fbe6
出典データセット
uspto-grants-2011_01
特許番号
US07872129B2

反応ノート

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