Potassium Hydroxide → 4,6-Diamino-5-(2-methoxybenzyl)-2-[2-(1-piperazinyl)ethylthio]-pyrimidine fumarate

HRID 992671ノート

反応式

HRID 992671 の反応式
[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16]C)=[C:6]([NH2:18])[N:5]=[C:4]([SH:19])[N:3]=1.[OH-].[K+].Cl.Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>O.C(O)C.CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[NH2:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([NH2:18])[N:5]=[C:4]([S:19][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[N:3]=1

参加物

8

反応物 4

HCID 14797Potassium HydroxideHCID 444972Fumaric AcidHCID 184131231-(2-Chloroethyl)piperazine dihydrochlorideHCID 178466178HCID 178466178、化合物

生成物 1

HCID 98055964,6-Diamino-5-(2-methoxybenzyl)-2-[2-(1-piperazinyl)ethylthio]-pyrimidine fumarate収率 94.6%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 887Methanol溶媒HCID 962Water溶媒3 回

実験手順

2.99 g (9.5 mmoles) of 4,6-diamino-2-mercapto-5-(2-ethoxy-benzyl)pyrimidine are suspended in a solution of 3.37 g (60 mmoles) of potassium hydroxide in 60 ml of water, and, to the suspension obtained, a solution of 2.22 g (10 mmoles) of 1-(2-chloroethyl)piperazine dihydrochloride in 10 ml of water are added, drop by drop, at 25° C. The reaction mixture is stirred at room temperature for 2 hours, then 50 ml of water and 100 ml of methyl alcohol are added. The mixture is heated to boiling point, filtered while hot, and the filtrate is allowed to crystallize at 0° C. The substance obtained is purified by chromatography over a column filled with 130 g of Kieselgel 60 using a mixture of methyl alcohol and toluene in a ratio of 2:3. The crystalline product obtained is recrystallized from a mixture of 20 ml of methyl alcohol and 20 ml of water to obtain 2.20 g of substance that is the dihydrate of the base. This compound is dissolved in 40 ml of ethyl alcohol under heating, and the solution obtained is added to a solution of 0.64 g of fumaric acid in 15 ml of ethyl alcohol. After crystallization at room temperature, 2.56 g (53%) of the title product are obtained. M.p.: 187-189° C.

後処理

  1. customto the suspension obtained
  2. customat 25° C
  3. temperatureThe mixture is heated
  4. filtrationfiltered while hot, and the filtrate
  5. customto crystallize at 0° C
  6. customThe substance obtained
  7. customis purified by chromatography over a column
  8. additionfilled with 130 g of Kieselgel 60 using
  9. additiona mixture of methyl alcohol and toluene in a ratio of 2:3
  10. customThe crystalline product obtained
  11. customis recrystallized from a mixture of 20 ml of methyl alcohol and 20 ml of water
  12. customto obtain 2.20 g of substance that
  13. temperatureunder heating
  14. customthe solution obtained
  15. customAfter crystallization at room temperature

出典と根拠

ORDレコード
ord-ddb52711e10a4da99e06d95a1972b90d
出典データセット
uspto-grants-2002_10
特許番号
US06469168B1

反応ノート

読み込み中…