Tetrahydrofuran → 3-(hydroxymethyl)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

HRID 1692915노트

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HRID 1692915 반응식
[C:1]([CH2:3][C:4]1([N:12]2[CH:16]=[C:15]([C:17]3[C:18]4[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH:14]=[N:13]2)[CH2:7][CH:6]([C:8](OC)=[O:9])[CH2:5]1)#[N:2].O1CCCC1.[BH4-].[Li+]>CO>[OH:9][CH2:8][CH:6]1[CH2:7][C:4]([CH2:3][C:1]#[N:2])([N:12]2[CH:16]=[C:15]([C:17]3[C:18]4[CH:25]=[CH:24][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH:14]=[N:13]2)[CH2:5]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 67017201methyl 3-(cyanomethyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutanecarboxylate

생성물 1

HCID 670172063-(hydroxymethyl)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

To a mixture of methyl 3-(cyanomethyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutanecarboxylate (7.0 g, 0.015 mol) in tetrahydrofuran (100 mL, 1 mol) was added lithium tetrahydroborate (0.327 g, 0.0150 mol) at 0° C. The reaction was then heated at 50° C. for 3 h. To the reaction was added 60 mL of methanol. The resulting mixture was heated at 50° C. for another 15 min, then evaporated to dryness. The residue was treated with 1 N HCl, then neutralized with solid sodium bicarbonate, extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 100% EtOAc, to give the desired product as cis- and trans-mixture (5.85 g, 88.91%). LCMS calculated for C22H31N6O2Si(M+H)+: 439.2; Found: 439.4.

후처리

  1. temperatureThe resulting mixture was heated at 50° C. for another 15 min
  2. customevaporated to dryness
  3. additionThe residue was treated with 1 N HCl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified on silica gel
  9. washeluting with 0 to 100% EtOAc

출처 및 근거

ORD 기록
ord-f60900ea81554745b9488314fd186932
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158616B2

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