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Hydrochloric Acid → 7H-Pyrrolo(2,3-d)pyrimidine-6-carboxamide, 2-amino-7-cyclopentyl-N,N-dimethyl-

HRID 1850610
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HRID 1850610 반응식
[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[N:27]([CH:28]([CH2:32]C)[CH2:29][CH2:30][CH3:31])[C:8]2[N:9]=[C:10]([N:13]=C(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].Cl.CCCCCCC.CCOC(C)=O>C1COCC1>[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[N:27]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[C:8]2[N:9]=[C:10]([NH2:13])[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 21899848Ethylacetate heptaneHCID 86686649HCID 86686649, 화합물

생성물 1

HCID 673553697H-Pyrrolo(2,3-d)pyrimidine-6-carboxamide, 2-amino-7-cyclopentyl-N,N-dimethyl-수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(benzhydrylidene-amino)-7-(1-ethyl-butyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (3.5 g, 8.0 mmol) in 26.7 mL THF was added aqueous 2M HCl (1.32 mL) and the mixture was stirred for 20 min. To this was added 60 mL heptane:EtOAc (4:1 v/v) and 60 mL aqueous 0.5N HCl and the layers were separated. The acidic aqueous layer was basified to pH 10 with aqueous 25% NaOH solution and extracted again with EtOAc. The organic extract was then washed with brine, dried (Na2SO4), concentrated and purified via SiO2 column chromatography (0-20% MeOH in EtOAc) to give 2-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a white solid (1.68 g, 6.15 mmol, 77% yield). MS m/z 274.4 (M+H)+.

후처리

  1. customthe layers were separated
  2. extractionextracted again with EtOAc
  3. extractionThe organic extract
  4. washwas then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via SiO2 column chromatography (0-20% MeOH in EtOAc)

출처 및 근거

ORD 기록
ord-f58b9d163ac24d13808c5fc471478b96
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957074B2

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