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

HRID 1910993
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HRID 1910993 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 2

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71c3a0bdecd9485ead8a9d409f8c44a5
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08604043B2

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