N-Iodosuccinimide → N4-(Cyclopropylmethyl)-5-iodopyrimidine-2,4-diamine

HRID 875977

反応式

HRID 875977 の反応式
[I:1]N1C(=O)CCC1=O.[CH:9]1([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:11][CH2:10]1>CC(O)=O>[CH:9]1([CH2:12][NH:13][C:14]2[C:19]([I:1])=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:10][CH2:11]1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 20277654N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

生成物 1

HCID 58299566N4-(Cyclopropylmethyl)-5-iodopyrimidine-2,4-diamine収率 60%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

N-iodosuccinimide (11.5 g, 50.9 mmol) was added to a solution of compound 237 (7.60 g, 46.3 mmol) in AcOH (90 mL). The reaction was warmed to 80° C. and stirred for 1.5 h. Solvent was removed in vacuo. The residue was taken up in dichloromethane (200 mL) and water. The aqueous layer was brought to pH 12 with 5 N NaOH and organics were sequestered. The aqueous was extracted further with dichloromethane (2×100 mL). The combined organics were treated with solid sodium thiosulfate, dried with MgSO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes) afforded compound 238 (8.0 g, 60% yield).

後処理

  1. customSolvent was removed in vacuo
  2. extractionThe aqueous was extracted further with dichloromethane (2×100 mL)
  3. additionThe combined organics were treated with solid sodium thiosulfate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-f1067da8d7604dfe8764f95885a2f7af
出典データセット
uspto-grants-2015_03
特許番号
US08980903B2

関連ノート

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