Maleic Acid → 1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine bis maleate

HRID 897467Notes

Reaction equation

HRID 897467 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C@@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:18]4=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]4[C:16]([C:24]4[CH:25]=[N:26][C:27]([O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[N:28][CH:29]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41]>C(O)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:18]4=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]4[C:16]([C:24]4[CH:25]=[N:26][C:27]([O:30][C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[N:28][CH:29]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178481011HCID 178481011, compound

Product 1

HCID 865862461-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine bis maleateYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (int AW) (0.193 g, 0.00040 mol) in absolute ethanol (15 mL) was heated to reflux. A solution of maleic acid (0.184 g, 0.00159 mol) in absolute ethanol (10 mL) heated to 78° C. was added and the mixture was heated at reflux for 10 minutes. The mixture was allowed to cool to room temperature, and the white precipitate which formed was collected by filtration and washed with absolute ethanol (2×10 mL). The residual solvent was removed in vacuo to give 1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine bis maleate as a white solid (0.254 g, 0.00035 mol):

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 10 minutes
  4. customthe white precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with absolute ethanol (2×10 mL)
  7. customThe residual solvent was removed in vacuo

Sources & evidence

ORD record
ord-6beb3bc9207b4cbca53b2aaf234ef029
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…