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

HRID 354887

반응식

HRID 354887 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:23][CH:24]=[C:25]([C:30](OC)=O)[C:26]([O:28][CH3:29])=[O:27].O>CN(C)C=O>[O:23]=[C:24]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:30]=[C:25]1[C:26]([O:28][CH3:29])=[O:27]

참가 물질

5

반응물 3

HCID 962WaterHCID 90770Dimethyl methoxymethylenemalonateHCID 130604654-Amino-6-(3-cyclopentylpropionamido)quinazoline

생성물 1

HCID 13060558methyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate수율 22.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-amino-6-(3-cyclopentylpropionamido)quinazoline (7.05 g) and dimethyl methoxymethylenepropanedioate (6.48 g) in N,N-dimethylformamide (28 ml) was stirred at 100° C. for 1 hour and 10 minutes. After cooling to ambient temperature, water was added to the reaction mixture. The resulting solid was separated by filtration, washed with water, and dried. The crude crystals were dissolved in a mixture of chloroform and methanol, treated with activated charcoal, and evaporated under reduced pressure until crystallization began. After cooling, the resulting solid was collected, washed with methanol and with dichloromethane, and dried. There was obtained crystalline methyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (2.16 g). The filtrate was evaporated under reduced pressure to give a residue which was chromatographed on silica gel with 1% methanoldichloromethane. The first fractions contained methyl 4-oxo-10-(3-cyclopentylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (1.9 g). The second fractions contained dimethyl [[6-(3-cyclopentylpropionamido)-4-quinazolinylamino]methylene]propanedioate (5.16 g).

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water
  4. customdried
  5. dissolutionThe crude crystals were dissolved in a mixture of chloroform and methanol
  6. additiontreated with activated charcoal
  7. customevaporated under reduced pressure until crystallization
  8. temperatureAfter cooling
  9. customthe resulting solid was collected
  10. washwashed with methanol and with dichloromethane
  11. customdried

출처 및 근거

ORD 기록
ord-ba116ebc72ef4018bfa5906de955ee09
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377580

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