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Triethylamine → 2-(Cyclopentylmethyl)-6-oxo-4-(3-pyridinylamino)-1,6-dihydro-5-pyrimidinecarbonitrile

HRID 1724649
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HRID 1724649 반응식
[C:1]([C:3](=[C:8](SC)[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6]C)=O)#[N:2].Cl.[CH:19]1([CH2:24][C:25]([NH2:27])=[NH:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CN(C=O)C.O>[CH:19]1([CH2:24][C:25]2[NH:27][C:4](=[O:6])[C:3]([C:1]#[N:2])=[C:8]([NH:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[N:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 68937763Methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoateHCID 689380642-Cyclopentylethanimidamide hydrochloride

생성물 1

HCID 1360559212-(Cyclopentylmethyl)-6-oxo-4-(3-pyridinylamino)-1,6-dihydro-5-pyrimidinecarbonitrile

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

0.1 g (0.40 mmol) of methyl 2-cyano-3-(methylsulfanyl)-3-(3-pyridinylamino)-2-propenoate and 0.065 g (0.40 mmol) of 2-cyclopentylethanamidine hydrochloride and 0.16 g (1.60 mmol) of triethylamine are dissolved in 0.5 ml of DMF and stirred at 100° C. overnight. After cooling, the mixture is diluted with 10 ml of water and extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated in vacuo, and the residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1). 78 mg (64% of theory) of the product are obtained as a colorless solid.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue is purified by flash chromatography (mobile phase: dichloromethane/methanol 200:1, 100:1, 50:1)
  6. custom78 mg (64% of theory) of the product are obtained as a colorless solid

출처 및 근거

ORD 기록
ord-5978ce1c15b648e08bc4f627ed4abec8
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07488733B2

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