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

HRID 1685178

反応式

HRID 1685178 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-598b35b6448f4efb9b4575838bdc202a
出典データセット
uspto-grants-2012_04
特許番号
US08148387B2

関連ノート

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