Methyl iodide → 7-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 988824ノート

反応式

HRID 988824 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]1([S:19]([N:22]2[C:26]3[N:27]=[CH:28][N:29]=[C:30]([Cl:31])[C:25]=3[CH:24]=[C:23]2[C:32]2C=CC=CC=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC>C1COCC1>[C:13]1([S:19]([N:22]2[C:26]3[N:27]=[CH:28][N:29]=[C:30]([Cl:31])[C:25]=3[CH:24]=[C:23]2[CH3:32])(=[O:21])=[O:20])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 224845527-Benzenesulfonyl-4-chloro6-phenyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 224844987-(Benzenesulfonyl)-4-chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To flame-dried flask under N2 was charged 0.57 ml (4.07 mmol) of diisopropylamine and 5.0 mL of dry THF. The solution was cooled to −78 OC and 1.63 mL (4.08 mmol) of a 2.5 M solution of n-butyllithium in hexanes added. The resulting mixture was brought to 0° C. and stirred for 10 minutes. After cooling the mixture again to −78° C., a solution of 1.0 g (3.40 mmol) of crude product from Method C in 10 mL of dry THF was added over a 10 minute period. The resulting mixture was stirred for 1 hour, at which time, 0.28 mL (4.50 mmol) of iodomethane were added. The reaction mixture was stirred for 2 hours, quenched with a saturated solution of NH4Cl and warmed to room temperature. The mixture was stirred for 5 minutes, diluted with water and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, filtered and evaporated in vacuo to obtain the title compound. LRMS: 308, 310 (M+2).

後処理

  1. customTo flame-dried flask under N2
  2. additionadded
  3. customwas brought to 0° C.
  4. additionwere added
  5. stirringThe reaction mixture was stirred for 2 hours
  6. customquenched with a saturated solution of NH4Cl
  7. temperaturewarmed to room temperature
  8. stirringThe mixture was stirred for 5 minutes
  9. additiondiluted with water
  10. extractionextracted three times with ethyl acetate
  11. washThe combined extracts were washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. customevaporated in vacuo

出典と根拠

ORDレコード
ord-1fa2777d887843899e08d69988165ce5
出典データセット
uspto-grants-2003_10
特許番号
US06635762B1

反応ノート

読み込み中…