N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)-N1,N2-bis[(4-methoxyphenyl)methyl]butane-1,2-diamine → N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)butane-1,2-diamine

HRID 333096노트

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HRID 333096 반응식
[CH2:1]([C:3]1[C:4]([N:10](CC2C=CC(OC)=CC=2)[CH:11]([CH2:23][CH3:24])[CH2:12][NH:13]CC2C=CC(OC)=CC=2)=[N:5][CH:6]=[N:7][C:8]=1[CH3:9])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[CH2:1]([C:3]1[C:4]([NH:10][CH:11]([CH2:23][CH3:24])[CH2:12][NH2:13])=[N:5][CH:6]=[N:7][C:8]=1[CH3:9])[CH3:2]

참가 물질

5

반응물 2

HCID 66835442N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)-N1,N2-bis[(4-methoxyphenyl)methyl]butane-1,2-diamineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 66835480N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)butane-1,2-diamine수율 287.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

N2-(5-Ethyl-6-methyl-pyrimidin-4-yl)-N1,N2-bis[(4-methoxyphenyl)methyl]butane-1,2-diamine (353 mg, 0.787 mmol) was dissolved in acetic acid (2 ml), the vial was flushed with argon, palladium (10% on activated carbon, 109 mg, 0.102 mmol) was added, and the mixture was stirred in an atmosphere of hydrogen at room temperature overnight. The mixture was filtered, the filter residue was washed with acetic acid, the combined filtrates were concentrated under reduced pressure to yield 472 mg of a brown oil. The residue was dissolved in DCM, washed with a saturated solution of sodium bicarbonate, the combined aqueous solutions were extracted three times with DCM. The organic phases were combined and concentrated under reduced pressure, the residue was purified by column chromatography (silica, gradient from DCM to a 9 to 1 mixture of DCM and 7N NH3 in methanol) to yield 94.6 mg of a yellow oil. The oil was dissolved in a mixture of diethylether and DCM, 1M HCl in diethylether was added until the product precipitated. The precipitate was isolated by decantation, washed with diethylether and dried in stream of nitrogen and under reduced pressure to give 127 mg of a white solid (0.498 mmol, 63%). MS (ESI) m/z=209.2 [M+1]+.

후처리

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. washthe filter residue was washed with acetic acid
  4. concentrationthe combined filtrates were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-073ec3c844794a1685f11b9c99f7232e
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877934B2

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