ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ammonium Hydroxide → 3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile

HRID 1910993
ノート
印刷プレビュー

反応式

HRID 1910993 の反応式
C[Si](C)(C)CC[O:5]C[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:22][C:23]#[N:24])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.F[B-](F)(F)F.[Li+].[OH-].[NH4+]>O.C(#N)C>[NH4+:7].[OH-:5].[N:12]1[C:11]2[NH:7][CH:8]=[CH:9][C:10]=2[C:15]([C:16]2[CH:17]=[N:18][N:19]([CH:21]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:22][C:23]#[N:24])[CH:20]=2)=[N:14][CH:13]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 14923Ammonium HydroxideHCID 4298216Lithium tetrafluoroborateHCID 595905383-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile

生成物 2

HCID 14923Ammonium Hydroxide収率 0.15%HCID 498192963-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile収率 147.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

Into a 500 mL round bottom flask fitted with stir bar, condenser and nitrogen inlet was charged acetonitrile (58 mL), water (5.0 mL), 3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]heptanenitrile (2nd peak from chiral separation in step 2, 3.50 g, 8.24 mmol), and lithium tetrafluoroborate (7.88 g, 82.4 mmol). The mixture was warmed to reflux overnight. To the reaction mixture was charged 7.2 M of ammonium hydroxide in water (4.3 mL, 31 mmol) in portions over a period of 5 minutes at room temperature adjusting pH to 9-10. The resulting reaction mixture was stirred for 2 hours at room temperature. Solid was removed by filtration and the filtrate was purified on RP-HPLC (XBridge column C18, 30×100 mm 5 μM; with injection volume 5 mL and flow rate 60 mL/min; at a gradient of water and acetonitrile and 0.15% NH4OH) to give desired product (1.79 g, 74%). LCMS calculated for C16H19N6(M+H)+: m/z=295.2. Found: 295.2.

後処理

  1. customInto a 500 mL round bottom flask fitted
  2. temperatureThe mixture was warmed
  3. temperatureto reflux overnight
  4. customThe resulting reaction mixture
  5. stirringwas stirred for 2 hours at room temperature
  6. customSolid was removed by filtration
  7. customthe filtrate was purified on RP-HPLC (XBridge column C18, 30×100 mm 5 μM

出典と根拠

ORDレコード
ord-71c3a0bdecd9485ead8a9d409f8c44a5
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08604043B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート