4-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)but-3-yn-1-ol → 4-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol

HRID 1972776ノート

反応式

HRID 1972776 の反応式
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]#[C:12][CH2:13][CH2:14][OH:15])[N:6]2[N:5]=[CH:4][N:3]=1>C(O)(=O)C.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[N:6]2[N:5]=[CH:4][N:3]=1

参加物

4

反応物 1

HCID 585295674-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)but-3-yn-1-ol

生成物 1

HCID 585292824-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol収率 91%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 176Acetic Acid溶媒

実験手順

To a dry flask purged with N2 was added platinum(IV) oxide (440 mg, 1.93 mmol) followed by 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)but-3-yn-1-ol (1.30 g, 6.43 mmol) as a solution in acetic acid (50 mL). The mixture was stirred under an H2 atmosphere for 16 h. The mixture was filtered through a pad of Celite®, rinsing with acetic acid and ethanol. The solvent was evaporated under reduced pressure and the residue was taken up in EtOAc (100 mL). The organic was washed with saturated aqueous NaHCO3 (1×100 mL) and the aqueous phase was back extracted with ethyl acetate (3×50 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness to afford the 1.2 g (91%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.77 (s, 1 H), 7.52 (br s, 2 H), 6.78 (d, 1 H), 6.39 (d, 1 H), 4.36 (br s, 1 H), 3.39 (t, 2 H), 2.81 (t, 2H), 1.72-1.61 (m, 2 H), 1.50-1.41 (m, 2 H); ES-MS m/z 207.2 [M+H]+, HPLC RT (min) 1.11.

後処理

  1. customTo a dry flask purged with N2
  2. filtrationThe mixture was filtered through a pad of Celite®
  3. washrinsing with acetic acid and ethanol
  4. customThe solvent was evaporated under reduced pressure
  5. washThe organic was washed with saturated aqueous NaHCO3 (1×100 mL)
  6. extractionthe aqueous phase was back extracted with ethyl acetate (3×50 mL)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-4a6d9096de784308a49f056f400a2c05
出典データセット
uspto-grants-2013_04
特許番号
US08431695B2

反応ノート

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