Cyclopropanemethanamine → 5-bromo-2-(cyclopropylmethylamino)-3-methylpyrimidin-4(3H)-one

HRID 2241239ノート

反応式

HRID 2241239 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.[CH:11]1([CH2:14][NH2:15])[CH2:13][CH2:12]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:15][CH2:14][CH:11]2[CH2:13][CH2:12]2)=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 75646CyclopropanemethanamineHCID 516892Sodium BicarbonateHCID 673486115-bromo-2-chloro-3-methylpyrimidin-4(3H)-one

生成物 1

HCID 685168835-bromo-2-(cyclopropylmethylamino)-3-methylpyrimidin-4(3H)-one収率 98.1%

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 (0.100 g, 0.45 mmol), cyclopropylmethanamine (0.051 mL, 0.58 mmol) and NaHCO3 (0.150 g, 1.79 mmol) in n-BuOH (3 mL) was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The EtOAc layer 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 (0.114 g, 98%) as a pale yellow solid that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.93 (s, 1H), 7.46 (t, J=5.5 Hz, 1H), 3.33 (s, 3H), 3.19 (t, J=6.2 Hz, 2H), 1.12 (m, 1H), 0.43 (m, 2H), 0.24 (m, 2H). LRMS (ESI pos) m/e 258, 260 (M+1, Br pattern).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe EtOAc layer 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-11a21765cc9243509ba21a2aafd09c8b
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

反応ノート

読み込み中…