Water → ethyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate

HRID 1719967

반응식

HRID 1719967 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:21])[CH2:14][CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O:24][CH:25]=[C:26]([C:32](OCC)=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])C.O>CN(C)C=O>[O:24]=[C:25]1[N:3]2[CH:4]=[N:5][C:6]3[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:21])[CH2:14][CH2:15][CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)=[CH:10][C:11]=3[C:2]2=[N:1][CH:32]=[C:26]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

참가 물질

5

반응물 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 130604654-Amino-6-(3-cyclopentylpropionamido)quinazoline

생성물 1

HCID 13060563ethyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate수율 38%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-amino-6-(3-cyclopentylpropionamido)-quinazoline (4.4 g) and diethyl ethoxymethylenepropanedioate (5.5 g) in N,N-dimethylformamide (20 ml) was stirred at 100° C. for 3 hours. To the reaction mixture was added water. The resulting crystals were collected by filtration, washed with water, and suspended in dichloroethane under heating. After the suspension was cooled to ambient temperature, the resulting crystals were collected by filtration and washed wit dichloromethane. There was obtained ethyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]-quinazoline-3-carboxylate (2.4 g). The filtrate was concentrated to 1/4 of its original volume and cooled to 0° C. to yield an additional 0.37 g of the same product. The cryde substance (2.77 g) obtained above was chromatographed on silica gel with 2% methanol-dichloromethane. The product was recrystallized from a mixture of methanol and dichloromethane to give crystalline pure product (2.45 g).

후처리

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with water
  3. temperatureunder heating
  4. temperatureAfter the suspension was cooled to ambient temperature
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed wit dichloromethane

출처 및 근거

ORD 기록
ord-9166bef1a4904d3ea91107c5e36f47e1
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04543356

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