Pyrimidine → Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate

HRID 1044074ノート

反応式

HRID 1044074 の反応式
[CH:1]1([NH:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1.N1C=CC=NC=1>CC(C)=O>[CH:1]1([N:6]([C:22]2[C:23]([N+:27]([O-:29])=[O:28])=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 9260PyrimidineHCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 28307099Methyl 3-(cyclopentylamino)propanoate

生成物 1

HCID 57940528Methyl 3-[cyclopentyl(2-chloro-5-nitropyrimidin-4-yl)amino]propanoate収率 65%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

Methyl 3-(cyclopentylamino)propanoate (838 mg, 0.005 mol) and K2CO3 (676 mg, 0.005 mol) were added to acetone (5 ml) and the resulting mixture cooled to 0° C. using an ice-bath before the addition of 2,4-dichloro-5-nitropyrimidine (1.044 g, 1.1 eq). The reaction mixture (RM) was then warmed to rt and stirring continued for an additional 16 h before the addition of a further 0.12 eq of the pyrimidine. Stirring was then continued for a further 3 h. The RM was then evaporated under reduced pressure and the product extracted using EtOAc/H2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give the product as a brown oily residue (1.04 g, 65%); Rt=16 min (Vydac 1); ME+ve: 329.1.

後処理

  1. temperatureThe reaction mixture (RM) was then warmed to rt
  2. stirringStirring
  3. customThe RM was then evaporated under reduced pressure
  4. extractionthe product extracted
  5. washwashed with sat NaCl
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate evaporated under reduced pressure
  9. customfurther dried in vacuo

出典と根拠

ORDレコード
ord-7dbc2e6b62ee4bb69e91e44ab23d4bd0
出典データセット
uspto-grants-2013_10
特許番号
US08563542B2

反応ノート

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