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Dimethyl Sulfoxide → 4-[4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopent-2-enol

HRID 51519
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HRID 51519 반응식
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:21]([NH2:23])=[N:20][CH:19]=[N:18][C:17]=3[NH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:26].[CH:28]1[CH2:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:23][C:21]1[C:22]2[C:14]([C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)=[CH:15][N:16]([CH:29]3[CH2:28][CH:32]([OH:26])[CH:31]=[CH:30]3)[C:17]=2[N:18]=[CH:19][N:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 679Dimethyl SulfoxideHCID 7612CyclopentadieneHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

생성물 1

HCID 227363204-[4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopent-2-enol

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (600 mg) and tetrakis(triphenylphosphine) palladium (40 ml) and dry dimethyl sulphoxide (30 ml) was stirred under nitrogen in an ice/water bath and then a solution of cyclopentadiene monoepoxide (200 mg) in tetrahydrofuran (10 ml) was added via syringe under nitrogen at 0° C. The mixture was stirred at ambient temperature (with exclusion of light) for 66 hours and then the tetrahydrofuran was removed under reduced pressure and water was added to the residue. The mixture was allowed to stand for 18 hours and then extracted with ethyl acetate to give a residue which was purified by flash column chromatography on silica using ethyl acetate/industrial methylated spirit (9:1) as the mobile phase to give 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopent-2-enol, as an oil. The structure was confirmed by 1Hnmr and mass spectra.

후처리

  1. stirringThe mixture was stirred at ambient temperature (with exclusion of light) for 66 hours
  2. customthe tetrahydrofuran was removed under reduced pressure and water
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. customto give a residue which
  6. customwas purified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-4bc18f45ebcd4c368e9c8ecbe58c78eb
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06713474B2

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