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(2-Nitrophenyl)acetic acid → 4,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidine

HRID 743975
ノート
印刷プレビュー

反応式

HRID 743975 の反応式
C(N(C(C)C)C(C)C)C.Cl.Cl.[C:12](=[NH:20])([O:18][CH3:19])[CH2:13][C:14](=[NH:17])[O:15][CH3:16].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](O)=O)([O-:23])=[O:22].C(C1NC=CN=1)(C1NC=CN=1)=O>ClCCl.CC(O)C>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([O:18][CH3:19])[N:20]=[C:31]([CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N+:21]([O-:23])=[O:22])[N:17]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 77337(2-Nitrophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 12896693Dimethyl malonimidate dihydrochloride

生成物 1

HCID 539772304,6-Dimethoxy-2-(2-nitrobenzyl)pyrimidine収率 32.9%

試薬・触媒・溶媒 2

HCID 3776
Isopropanol
溶媒
HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-40 °C

実験手順

Ethyl diisopropylamine (240 ml) was added dropwise to a stirred suspension of dimethyl malonimidate dihydrochloride (73.2 g) in dichloromethane (400 ml) at -40° C. under nitrogen, and the mixture was stirred at -40° C. for 25 minutes to give suspension A. 2-Nitrophenylacetic acid (65.16 g) was added portionwise to a stirred suspension of carbonyl diimidazole (53.3 g) in dichloromethane (400 ml) at room temperature. The resulting solution was stirred for 10 minutes and was added dropwise over 30 minutes to the suspension A at -40° C. The mixture was stirred at -40° C. for a further 45 minutes and then at room temperature overnight, after which the solution was washed with water (400 ml), 2N HCl (400 ml) and saturated sodium bicarbonate solution (400 ml), dried and evaporated to give an orange solid. It was then stirred with propan-2-ol (50 ml) for 10 minutes and filtered. The solid was washed with a further 50 ml of propan-2-ol and then dried to give 32.6 g of the desired product as a yellow solid, mp 92°-93° C.

後処理

  1. customto give suspension A
  2. stirringThe resulting solution was stirred for 10 minutes
  3. additionwas added dropwise over 30 minutes to the suspension A at -40° C
  4. stirringThe mixture was stirred at -40° C. for a further 45 minutes
  5. washat room temperature overnight, after which the solution was washed with water (400 ml), 2N HCl (400 ml) and saturated sodium bicarbonate solution (400 ml)
  6. customdried
  7. customevaporated
  8. customto give an orange solid
  9. filtrationfiltered
  10. washThe solid was washed with a further 50 ml of propan-2-ol
  11. customdried

出典と根拠

ORDレコード
ord-6bc8715185bf4c238d04bac23d77e81c
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05559081

反応ノート

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