Phosphorus oxychloride → 4-chloro-1-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1098203ノート

反応式

HRID 1098203 の反応式
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:23])=[C:11]([N:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=O)[C:16]=3[CH:15]=[N:14]2)[CH:12]=1>>[Cl:3][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:13]([C:11]3[CH:12]=[C:7]([F:6])[CH:8]=[CH:9][C:10]=3[CH3:23])[N:14]=[CH:15][C:16]=12

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 1360373241-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

生成物 1

HCID 574386624-chloro-1-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine収率 95.4%

反応条件

温度
100 °C

実験手順

Phosphorus oxychloride (5442 μl, 58.39 mmol) was added to 1-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (Intermediate AK2) (713 mg, 2.92 mmol), at ambient temperature. The resulting mixture was heated to 100° C. and stirred for 4 hours. The mixture was allowed to cool to ambient temperature. The reaction mixture was evaporated to near dryness. Dissolved into toluene, evaporated, dissolved, in toluene and evaporated to dryness again. The solid was dried under vacuum to give crude product. This was partitioned between EtOAc (70 mL), and water (25 mL). The organic phase was dried (MgSO4), evaporated, then dried under vacuum to afford the product (732 mg, 95%). 1H NMR (400 MHz, DMSO) δ 2.13 (3H, s), 7.52-7.42 (2H, m), 7.64-7.58 (1H, m), 8.83 (1H, s), 8.96 (1H, s); m/z (ES+) (M+H)+=263; HPLC tR=2.39 min.

後処理

  1. temperatureto cool to ambient temperature
  2. customThe reaction mixture was evaporated
  3. dissolutionDissolved into toluene
  4. customevaporated
  5. dissolutiondissolved, in toluene
  6. customevaporated to dryness again
  7. customThe solid was dried under vacuum
  8. customto give crude product
  9. customThis was partitioned between EtOAc (70 mL), and water (25 mL)
  10. dry with materialThe organic phase was dried (MgSO4)
  11. customevaporated
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-e232ddf316624d948fde3a9b245d208e
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

反応ノート

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