Iodine → 4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1365781

反応式

HRID 1365781 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([Li])CCC.[I:22]I>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:10]=[C:9]([I:22])[S:8][C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 807IodineHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholineHCID 178418339Butyllithium

生成物 1

HCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 4-(5-chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 dissolved in THF at −78° C. was added 1.6M solution of n-butyllithium in hexanes). The reaction mixture was stirred at −78° C. for 30 minutes. A solution of iodine in THF was added and reaction mixture was allowed to slowly warm up to room temperature and stirred for 45 minutes. The reaction mixture was quenched with saturated aq. Na2S2O3, and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The crude reaction mixture was purified by flash chromatography to yield 4-(5-chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18.

後処理

  1. customreaction mixture
  2. temperatureto slowly warm up to room temperature
  3. stirringstirred for 45 minutes
  4. customThe reaction mixture was quenched with saturated aq. Na2S2O3
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude reaction mixture
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-9d4b888d482e4e0bab634316bb35d1ed
出典データセット
uspto-grants-2011_02
特許番号
US07893059B2

関連ノート

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