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

HRID 1365781

반응식

HRID 1365781 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9d4b888d482e4e0bab634316bb35d1ed
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893059B2

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