Sodium cyanoborohydride → 4,5-Dihydro-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 2073185ノート

反応式

HRID 2073185 の反応式
[C:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[C:11]3[NH:10][CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 145018607-Phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide

生成物 1

HCID 1358568134,5-Dihydro-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A 6.0 g amount of 7-phenylpyrazolo[1,5-a]-pyrimidine-3-carboxamide (prepared as described in Example 2) was stirred under nitrogen as a suspension in 120 ml of glacial acetic acid (cooled in an ice bath) and then 3.5 g of sodium cyanoborohydride was added to the reaction mixture in portions. After one hour of stirring in the ice bath, the mixture was stirred at room temperature for 3.5 hours at which time the original solid dissolved. Stirring was continued for one hour longer then the solution was concentrated in vacuo. Water was added to the residue and a precipitate formed. The precipitate was collected by filtration and then was dissolved in dichloromethane. The organic solution was washed with a saturated solution of sodium bicarbonate, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give a solid. The solid was recrystallized from isopropyl alcohol to give 5.0 g of the desired product as a white solid, m.p. 149°-152° C.

後処理

  1. dissolutiondissolved
  2. stirringStirring
  3. waitwas continued for one hour
  4. concentrationlonger then the solution was concentrated in vacuo
  5. additionWater was added to the residue
  6. customa precipitate formed
  7. filtrationThe precipitate was collected by filtration
  8. dissolutionwas dissolved in dichloromethane
  9. washThe organic solution was washed with a saturated solution of sodium bicarbonate
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated in vacuo
  13. customto give a solid
  14. customThe solid was recrystallized from isopropyl alcohol

出典と根拠

ORDレコード
ord-3877960101db46d09a2afeeee165eaa7
出典データセット
uspto-grants-1990_04
特許番号
US04916137

反応ノート

読み込み中…