Triethylamine → HCID 178418609、化合物

HRID 6527

反応式

HRID 6527 の反応式
I[N:2]1[C:7]([OH:8])=[C:6]2[CH:9]=[C:10]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[N:11]=[C:5]2[N:4]=[CH:3]1.[CH2:19]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[C:20]#[CH:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[Pd](Cl)Cl.C(#N)C>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH2:19][C:20]#[C:21][N:2]1[C:7]([OH:8])=[C:6]2[CH:9]=[C:10]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[N:11]=[C:5]2[N:4]=[CH:3]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran2 回HCID 178418587HCID 178418587、化合物

生成物 1

HCID 178418609HCID 178418609、化合物

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 14.6 g of 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 7.6 g of 2-(2-propynyloxy)-tetrahydropyran, 798 mg (10%) of palladium chloride, 2.36 g (20%) of triphenyl phosphine, 428 mg (5%) of cuprous iodide, 45 ml of triethyl amine and 700 ml of acetonitrile is heated at reflux under nitrogen for 12 hours. There then are added to the hot reaction mixture 3.2 g of 2-(2-propynyloxy)-tetrahydropyran and reflux is continued for an additional 12 hours. After heating for a total of 24 hours under reflux, the solvent is removed under reduced pressure, and the residue filtered through silica gel using 2% methanol in methylene chloride. This filtrate is concentrated and chromatographed on silica gel eluting with 20:1 ethyl acetate:hexane mixture to give 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which is further purified by recrystallization with ethyl acetate.

後処理

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 12 hours
  3. temperaturereflux
  4. temperatureAfter heating for a total of 24 hours
  5. temperatureunder reflux
  6. customthe solvent is removed under reduced pressure
  7. filtrationthe residue filtered through silica gel using 2% methanol in methylene chloride
  8. concentrationThis filtrate is concentrated
  9. customchromatographed on silica gel eluting with 20:1 ethyl acetate

出典と根拠

ORDレコード
ord-e88b6018253240189f556b5baaee75e8
出典データセット
uspto-grants-1993_09
特許番号
US05248775

関連ノート

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