Hydrogen Bromide → HCID 11564642、化合物

HRID 895108ノート

反応式

HRID 895108 の反応式
CO[CH:3](OC)[CH2:4]Br.Br.C(=O)([O-])O.[Na+].[NH2:14][C:15]1[C:16](=[O:24])[N:17]([CH3:23])[C:18]([S:21][CH3:22])=[N:19][N:20]=1>CC(O)C.CO.O>[CH3:23][N:17]1[C:16](=[O:24])[C:15]2=[N:14][CH:3]=[CH:4][N:20]2[N:19]=[C:18]1[S:21][CH3:22]

参加物

8

反応物 4

HCID 260Hydrogen BromideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 115428516-Amino-4-methyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one

生成物 1

HCID 11564642HCID 11564642、化合物収率 47.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

Bromoacetaldehyde dimethyl acetal (2.57 g, 13.1 mmol), 48% hydrobromic acid (1.06 g, 13.1 mmol) and water (1.5 ml) were heated at 95° C. for 1.5 h. The mixture was allowed to cool to ambient temperature, diluted with propan-2-ol (20 ml) then treated with sodium hydrogen-carbonate (1.46 g, 17.4 mmol) added in portions over 5 min. The mixture was filtered and the filtrate was added to 6-amino-4-methyl-3-methylsulfanyl-4H-[1,2,4]triazin-5-one (1.50 g, 8.71 mmol). The resulting suspension was heated at 95° C. for 18 h. The mixture was allowed to cool to ambient temperature, diluted with methanol (100 ml) and evaporated onto silica. The product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%). Collecting appropriate fractions gave 3-methyl-2-methylsulfanyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one (0.81 g, 47%) as a pale yellow solid: δH (400 MHz, CDCl3) 2.61 (3H, s), 3.58 (3H, s), 7.49 (1H, d, J1), 7.52 (1H, d, J1).

後処理

  1. additionadded in portions over 5 min
  2. filtrationThe mixture was filtered
  3. temperatureThe resulting suspension was heated at 95° C. for 18 h
  4. temperatureto cool to ambient temperature
  5. customevaporated onto silica
  6. customThe product was purified by flash column chromatography on silica eluting with dichloromethane (+0.1% 0.880 ammonia) on a gradient of methanol (3-6%)
  7. customCollecting appropriate fractions

出典と根拠

ORDレコード
ord-e08e8b942b9947eebdad846b05b4f39a
出典データセット
uspto-grants-2005_07
特許番号
US06914060B2

反応ノート

読み込み中…