Sodium cyanoborohydride → 1,2-Dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199953ノート

反応式

HRID 1199953 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[CH:15]=[N:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 146774714-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide

生成物 1

HCID 146774841,2-Dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carboxamide収率 75.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 9.2 g of 4-(α,α,α-trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carboxamide (Ex. 28, U.S. Pat. No. 4,236,005) in 100 ml of glacial acetic acid, was added in portions 3.0 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated in vacuo to give an oil. The oil was triturated with water and a white precipitate formed, and this was collected by filtration, washed with water and then was slurried with saturated sodium bicarbonate solution. The precipitate was again collected by filtration and washed with water. This solid was dissolved in dichloromethane, and then water was added. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave a yellow solid which was recrystallized from acetonitrile to give 7.0 g of the product of the example as a light yellow solid, mp 192°-194° C.

後処理

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil
  3. customThe oil was triturated with water
  4. customa white precipitate formed
  5. filtrationthis was collected by filtration
  6. washwashed with water
  7. filtrationThe precipitate was again collected by filtration
  8. washwashed with water
  9. dissolutionThis solid was dissolved in dichloromethane
  10. additionwater was added
  11. customThe organic layer was separated
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customEvaporation of the filtrate
  15. customgave a yellow solid which
  16. customwas recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-f5ba5edbb6884655b74374313803de24
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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