5-Aminoimidazole-4-carboxamide hydrochloride → 4-(2,5-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199943

反応式

HRID 1199943 の反応式
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:19](=O)[CH:20]=[CH:21]N(C)C.C(=O)(O)[O-].[Na+].ClCCl.CCCCCC>C(O)(=O)C.ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:19]1[N:4]2[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]2[N:2]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 28062062',5'-Dichloro-3-dimethylaminoacrylophenoneHCID 21226440Methylenechloride Hexane

生成物 1

HCID 146774734-(2,5-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide収率 74.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

A stirred mixture of 5.2 g of 4-amino-5-imidazolecarboxamide hydrochloride and 10.0 g of 2',5'-dichloro-3-dimethylaminoacrylophenone (prepared as described in Example 4) in 80 ml of glacial acetic acid was heated at reflux for 4 hours. Evaporation in vacuo gave a dark oil which was dissolved in dichloromethane and treated with saturated sodium bicarbonate. The organic layer was separated, washed with water then dried over anhydrous sodium sulfate. The dichloromethane solution was passed through a short column of hydrous magnesium silicate. Evaporation of the eluate gave a semi-solid which was treated with hot dichloromethane-hexane to give a yellow precipitate which was collected by filtration and dried to give 7.3 g of the product of the example, mp 230°-234° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customEvaporation in vacuo
  4. customgave a dark oil which
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialthen dried over anhydrous sodium sulfate
  8. customEvaporation of the eluate
  9. customgave a semi-solid which
  10. customto give a yellow precipitate which
  11. filtrationwas collected by filtration
  12. customdried

出典と根拠

ORDレコード
ord-f5b3f9f1af7b4d62b7b9c7a11cbb4212
出典データセット
uspto-grants-1990_02
特許番号
US04904658

関連ノート

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