Tin tetrachloride → HCID 118294255、化合物

HRID 2205181ノート

反応式

HRID 2205181 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][NH:5][C:4](=[O:9])[N:3]=1.C(O[CH:14]1[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([CH:31]([F:33])[F:32])[O:15]1)(=O)C.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>CC#N>[C:20]([O:19][C@@H:18]1[C@H:17]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:16]([CH2:34][O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH:31]([F:32])[F:33])[O:15][C@H:14]1[N:5]1[CH:6]=[C:7]([Cl:8])[C:2]([NH2:1])=[N:3][C:4]1=[O:9])(=[O:22])[CH3:21]

参加物

6

反応物 4

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 131735802HCID 131735802、化合物HCID 178509020HCID 178509020、化合物

生成物 1

HCID 118294255HCID 118294255、化合物収率 37.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
25 °C

実験手順

To a solution of 4-amino-5-chloropyrimidin-2(1H)-one 28 (0.336 g, 2.33 mmol) in anhydrous CH3CN (10 mL) was added BSA (0.945 g, 4.64 mmol) portion-wise while maintaining the reaction temperature at 25° C. After the reaction mixture became clear, compound 5 (0.54 g, 1.16 mmol) in CH3CN (2 mL) and SnCl4 (1.2 g, 4.64 mmol) was added into the mixture. The mixture was stirred at 65° C. for 1 h, then cooled and poured into saturated NaHCO3 solution (20 mL). The organic phase was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by flash silica gel chromatography [dichloromethane:methanol (40:1)] gave 29 as a white solid (0.24 g, 31%). LC-MS: (M+H)+=550.1

後処理

  1. temperaturecooled
  2. extractionThe organic phase was extracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness under reduced pressure
  6. customPurification by flash silica gel chromatography [dichloromethane:methanol (40:1)]

出典と根拠

ORDレコード
ord-51ae9e32612e44d198053b5bbe07ebe2
出典データセット
uspto-grants-2016_06
特許番号
US09370569B2

反応ノート

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