Imidazole → HCID 68469741、化合物

HRID 1889610ノート

反応式

HRID 1889610 の反応式
N1(O[C:11]2[C:12]3[N:13]=[CH:14][N:15]([C:38]=3[N:39]=[CH:40][N:41]=2)[C@@H:16]2[O:37][C@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:18]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:17]2)C2C=CC=CC=2N=N1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:48]1[CH:52]=[CH:51][N:50]=[CH:49]1>COCCOC>[N:48]1([C:11]2[N:41]=[CH:40][N:39]=[C:38]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:16]2[O:37][C@H:27]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[C@@H:18]([O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21])[CH2:17]2)[CH:52]=[CH:51][N:50]=[CH:49]1

参加物

5

反応物 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 24805984HCID 24805984、化合物

生成物 1

HCID 68469741HCID 68469741、化合物収率 60.3%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

In a clean, dry reaction vial equipped with a stirring bar were placed O6-(benzotriazol-1-yl)-2′,3′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyinosine (26) (59.8 mg, 0.100 mmol), Cs2CO3 (65.2 mg, 0.200 mmol) and imidazole (13.6 mg, 0.200 mmol). Dry DME (1.0 mL) was added and the reaction mixture was flushed with N2 and the mixture was allowed to stir at 85° C. for 4 h. The reaction mixture was concentrated and the residue was dissolved in EtOAc. The mixture was washed with water, dried over Na2SO4, and evaporated to dryness. Chromatographic purification (SiO2, elution with 50% EtOAc in hexanes) afforded 32.0 mg (60% yield) of the title compound as a clear gum. Rf (20% EtOAc in hexanes)=0.07. 1H NMR (500 MHz, CDCl3): δ 9.19 (s, 1H, Ar—H), 8.77 (s, 1H, Ar—H), 8.48 (s, 1H, Ar—H), 8.40 (s, 1H, Ar—H), 7.25 (s, 1H, Ar—H), 6.56 (t, 1H, H-1′, J=6.3), 4.64 (app q, 1H, H-3′, Japp˜4.2), 4.06 (m, 1H, H-4′), 3.90 (dd, 1H, J=11.2, 3.9), 3.80 (dd, 1H, H-5′, J=11.2, 2.9), 2.65 (app quint, 1H, H-2′, Japp˜6.3), 2.51 (m, 1H, H-2′), 0.92, 0.915 (2 s, 18H, tert-Bu), 0.11, 0.10 (2 s, 12H, SiCH3). 13C NMR (126 MHz, CDCl3): δ 153.0, 152.1, 145.6, 143.0, 137.7, 130.6, 122.9, 117.3, 88.1, 84.7, 71.7, 62.6, 41.5, 25.9, 25.7, 18.4, 18.0, −4.7, −4.8, −5.4, −5.5.

後処理

  1. customIn a clean, dry
  2. customreaction
  3. customvial equipped with a stirring bar
  4. customthe reaction mixture was flushed with N2
  5. concentrationThe reaction mixture was concentrated
  6. dissolutionthe residue was dissolved in EtOAc
  7. washThe mixture was washed with water
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customChromatographic purification (SiO2, elution with 50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-240e16fbfdcf48a597927fd303f90c6e
出典データセット
uspto-grants-2013_08
特許番号
US08501931B2

反応ノート

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