N-Iodosuccinimide → 5-iodo-4-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 509930ノート

反応式

HRID 509930 の反応式
[CH3:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[I:11]N1C(=O)CCC1=O>ClCCl>[I:11][C:10]1[C:3]2[C:2]([CH3:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 513419594-Methyl-7H-pyrrolo(2,3-d)pyrimidine

生成物 1

HCID 582592995-iodo-4-methyl-7H-pyrrolo[2,3-d]pyrimidine収率 76.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 4-methyl-7H-pyrrolo[2,3-d]pyrimidine (18, 0.634 g, 4.76 mmol) in 50 mL of dichloromethane, N-iodosuccinimide (1.3 g, 5.7 mmol) was added and the reaction stirred at room temperature for 45 minutes. The reaction was concentrated under vacuum, then ethyl acetate was added and washed with 1 N aqueous sodium thiosulfate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (19, 0.94 g). MS (ESI) [M+H+]+=260.26.

後処理

  1. concentrationThe reaction was concentrated under vacuum
  2. additionethyl acetate was added
  3. washwashed with 1 N aqueous sodium thiosulfate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was purified by silica gel column chromatography
  8. washeluting with 20-100% ethyl acetate in hexane
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-96a101577cbc4cb9bc9cede27d7906fd
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

読み込み中…