Sodium Thiosulfate → Methyl 3-amino-6-iodopyrazine-2-carboxylate

HRID 272053

反応式

HRID 272053 の反応式
[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[I:12]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[CH3:11][O:10][C:8]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([I:12])[N:4]=1)=[O:9]

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 120273N-Iodosuccinimide

生成物 1

HCID 11087124Methyl 3-amino-6-iodopyrazine-2-carboxylate収率 61.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Methyl 3-amino-2-pyrazinecarboxylate (10 g, 65.3 mmol) and N-iodosuccinimide (24 g, 106.7 mmol) were dissolved in anhydrous DMF (150 mL) and the mixture was stirred at 70° C. for 15 hours under a nitrogen atmosphere. The mixture was then cooled to room temperature and a saturated aqueous solution of sodium thiosulfate (400 mL) was added. The suspension was sonicated for 15 minutes, concentrated under vacuum and dispersed in water. The crude product was filtered off and washed with cold ethanol. The residue was crystallized from ethanol, using decolorizing charcoal to afford 3-amino-6-iodo-pyrazine-2-carboxylic acid methyl ester (11.2 g, 61% yield) as orange needles. 1H-NMR (d6-DMSO) δ: 8.57 [1H] s, 7.59 [2H] s,br, 3.93 [3H] s. MS: m/z 280 [MH+].

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe suspension was sonicated for 15 minutes
  3. concentrationconcentrated under vacuum
  4. additiondispersed in water
  5. filtrationThe crude product was filtered off
  6. washwashed with cold ethanol
  7. customThe residue was crystallized from ethanol

出典と根拠

ORDレコード
ord-57810c7f678345f98e9ba23883ec6ff3
出典データセット
uspto-grants-2008_11
特許番号
US07452993B2

関連ノート

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