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

HRID 354887

反応式

HRID 354887 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba116ebc72ef4018bfa5906de955ee09
出典データセット
uspto-grants-1983_03
特許番号
US04377580

関連ノート

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