Triethylamine → HCID 178418609, 화합물

HRID 6527

반응식

HRID 6527 반응식
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

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran2회HCID 178418587HCID 178418587, 화합물

생성물 1

HCID 178418609HCID 178418609, 화합물

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e88b6018253240189f556b5baaee75e8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248775

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