Iodine → 2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine

HRID 390815노트

반응식

HRID 390815 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[O:10][CH:9]=[CH: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[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][C:9]([I:22])=[CH:8][C:6]=2[N:7]=1

참가 물질

5

반응물 3

HCID 807IodineHCID 568337412-Chloro-4-morpholinofuro[3,2-d]pyrimidineHCID 178418339Butyllithium

생성물 1

HCID 595930702-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (50 mg, 1.0 eq) dissolved in THF (2.1 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.17 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. A solution of iodine (159 mg, 3.0 eq) in THF (0.6 ml) 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 2-chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine 45 (63 mg, 83%): MS (Q1) 366 (M)+.

후처리

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

출처 및 근거

ORD 기록
ord-5299dac637004dddb28ea8a72459849e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383620B2

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