Sodium cyanoborohydride → 4-(3-Chlorophenyl)-1,2-dihydroimidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199954ノート

反応式

HRID 1199954 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[CH:14]=[N:15][C:16]([C:17]([NH2:19])=[O:18])=[C:12]3[NH:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 146774724-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

生成物 1

HCID 146774854-(3-Chlorophenyl)-1,2-dihydroimidazo[1,5-a]pyrimidine-8-carboxamide収率 59.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5.39 g of 4-(m-chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide (Example 14) in 100 ml of glacial acetic acid, was added in portions 2.8 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 2 hours. The solvent was evaporated in vacuo to give an oil, and this was dissolved in dichloromethane, then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and filtered through a short column of hydrous magnesium silicate. Evaporation of the solvent gave a yellow solid which was recrystallized from acetonitrile to give 3.25 g of the desired product as a yellow solid, mp 182°-184° C.

後処理

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of hydrous magnesium silicate
  7. customEvaporation of the solvent
  8. customgave a yellow solid which
  9. customwas recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-bab6e77ff26c432b9557443259528f46
出典データセット
uspto-grants-1990_02
特許番号
US04904658

反応ノート

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