1,4-Diiodobutane → 4'-Chlorospiro[cyclopentane-1,5'-pyrrolo[2,3-d]pyrimidin]-6'(7'H)-one

HRID 1685178

반응식

HRID 1685178 반응식
[Cl:1][C:2]1[C:3]2[CH2:10][C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].I[CH2:23][CH2:24][CH2:25][CH2:26]I>C1COCC1>[Cl:1][C:2]1[C:3]2[C:10]3([CH2:26][CH2:25][CH2:24][CH2:23]3)[C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 123371,4-DiiodobutaneHCID 2733832Lithium HexamethyldisilazideHCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-one

생성물 1

HCID 593224014'-Chlorospiro[cyclopentane-1,5'-pyrrolo[2,3-d]pyrimidin]-6'(7'H)-one수율 43.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Add 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.6 g; 0.0035 mol; 1.0 equiv) in anhydrous THF (20 mL) and cool the reaction to −78° C., under an inert atmosphere. Add drop-wise lithium hexamethyldisilazide (8.8 mL; 0.0088 mol; 2.5 equiv; 1M in THF). Stir at −78° C. for 30 min. Add drop-wise 1,4-diiodobutane (0.56 mL; 0.0042 mol; 1.2 equiv), allow the reaction temperature to reach 0° C. slowly, and stir for 2 h. Then allow the reaction to reach RT and stir for additional 1 h. Quench the reaction with saturated ammonium chloride solution and extract with EA. Wash the organic layer with water, brine, and dry over anhydrous sodium sulfate. Evaporate the organic layer and purify over a 10 g silica column with acetone (5%) in DCM. Pool fractions to give the title compound (0.34 g; 43.09%). H NMR (DMSO-d6): 11.68 (1H, s), 8.53 (1H, s), 2.0-2.1 (m, 2H), 1.91-1.99 (m, 6H).

후처리

  1. temperaturecool
  2. customthe reaction to −78° C.
  3. customto reach 0° C.
  4. stirringstir for 2 h
  5. customthe reaction
  6. customto reach RT
  7. stirringstir for additional 1 h
  8. customQuench
  9. customthe reaction with saturated ammonium chloride solution
  10. extractionextract with EA
  11. washWash the organic layer with water, brine
  12. dry with materialdry over anhydrous sodium sulfate
  13. customEvaporate the organic layer
  14. custompurify over a 10 g silica column with acetone (5%) in DCM

출처 및 근거

ORD 기록
ord-598b35b6448f4efb9b4575838bdc202a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148387B2

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