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

HRID 477450

反応式

HRID 477450 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-b4225ec8f3b146fb9fffca1c71b90481
出典データセット
uspto-grants-1989_12
特許番号
US04888345

関連ノート

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