1,8-Diazabicyclo(5.4.0)undec-7-ene → 1,6-Naphthyridine-8-methanol

HRID 1861680ノート

反応式

HRID 1861680 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.C1C=CC(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)=CC=1.[CH2:30]1[CH2:40][CH2:39][N:38]2[C:33](=[N:34][CH2:35][CH2:36][CH2:37]2)[CH2:32][CH2:31]1>CCOC(C)=O>[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[N:27]([CH2:30][C:40]1[CH:39]=[N:38][CH:37]=[C:36]2[C:35]=1[N:34]=[CH:33][CH:32]=[CH:31]2)=[N+:28]=[N-:29]

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene3 回HCID 199401P,P-Diphenylphosphinic azide3 回HCID 120187001,6-Naphthyridine-8-methanol

生成物 2

HCID 120187001,6-Naphthyridine-8-methanolHCID 12018701HCID 12018701、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.93 g (5.8 mmol) 8-hydroxymethyl-1,6-napthyridine in 20 mL TBF was added 1.5 mL (7 mmol) DPPA and 1.2 mL (6.7 mmol) DBU. The reaction mixture was allowed to stir at room temperature 18 hours, then another 0.3 mL DPPA and 0.25 mL DBU were added and the reaction mixture heated to 50° C. for 8 hours then cooled to room temperature then another 0.3 mL DPPA and 0.25 mL DBU were added and the reaction mixture was allowed to stir 18 more hours at room temperature. The resulting solution was then diluted with 200 L EtOAc, washed with saturated NaHCO3 solution, and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (40×120 mm silica gel, linear gradient 2-15% MeOH:CH2Cl2) yielded 8-hydroxymethyl-1,6-napthyridine and 8-azidomethyl-1,6-napthyridine. 1H NMR (CDCl3, 400 MHz) δ 9.30 (s, 1H); 9.16 (dd, 1H, J=4.3 and 1.8 Hz); 8.78 (s, 1H); 8.35 (dd, 1H, J=8.3 and 1.74 Hz); 7.61 (dd, 1H, J=8.3 and 4.3 Hz); 5.00 (s, 2H).

後処理

  1. temperaturethe reaction mixture heated to 50° C. for 8 hours
  2. temperaturethen cooled to room temperature
  3. stirringto stir 18 more hours at room temperature
  4. washwashed with saturated NaHCO3 solution, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (40×120 mm silica gel, linear gradient 2-15% MeOH:CH2Cl2)

出典と根拠

ORDレコード
ord-a92165798b7f42ebbaacd136be1add68
出典データセット
uspto-grants-2003_03
特許番号
US06534510B2

反応ノート

読み込み中…