Aniline → 5-bromo-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

HRID 1676334ノート

反応式

HRID 1676334 の反応式
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](Cl)=[N:6][CH:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCCCO.CCOC(C)=O>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 673486115-bromo-2-chloro-3-methylpyrimidin-4(3H)-one

生成物 1

HCID 673454265-bromo-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one収率 99.5%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5-bromo-2-chloro-3-methylpyrimidin-4(3H)-one (0.510 g, 2.282 mmol), aniline (0.271 ml, 2.967 mmol) and NaHCO3 (0.767 g, 9.129 mmol) in n-BuOH (15 mL) was stirred at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer was washed with H2O and saturated aqueous NaCl. The aqueous phase was re-extracted with EtOAc (1×). The combined EtOAc layers were dried (Na2SO4), filtered and concentrated to yield the desired product (0.636 g, 99%) as a pale yellow solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.95 (br s, 1H), 7.94 (s, 1H), 7.47 (m, 2H), 7.35 (m, 2H), 7.14 (m, 1H), 3.53 (s, 3H). LRMS (ESI pos) m/e 280, 281 (M+, Br pattern).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe EtOAc layer was washed with H2O and saturated aqueous NaCl
  3. extractionThe aqueous phase was re-extracted with EtOAc (1×)
  4. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-164d2f6984ed4f8d8385e3c3dd543262
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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