HCID 59493237, compound → HCID 25227445, compound

HRID 1893174Notes

Reaction equation

HRID 1893174 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:22][CH2:21]3)[N:17]=[C:16]([NH2:33])[N:15]=2)=[CH:9][CH:8]=1)C>O1CCCC1.O.[K]>[NH2:33][C:16]1[N:15]=[C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:41])([O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:4]([OH:42])=[O:3])=[CH:8][CH:9]=2)[CH:19]=[C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:21]2)[N:17]=1

Participants

4

Reactant 1

HCID 59493237HCID 59493237, compound

Product 1

HCID 25227445HCID 25227445, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5347118072414-64-3Solvent

Procedure

3-{4-[2-Amino-6-(4-benzyl-piperazin-1-yl)-pyrimidin-4-yloxy]-phenyl}-2-methyl-2-phenoxy-propionic acid ethyl ester was dissolved in tetrahydrofuran (THF)/alcohol solvent in the presence of an excess of aqueous potassium hydrate, the reaction is allowed to proceed for about 20 h. After most of the solve was removed in vacuo, the aqueous solution was acidified to pH 6, the white product was precipitated, then filtered through celite, rac-3-{4-[2-Amino-6-(4-benzyl-piperazin-1-yl)-pyrimidin-4-yloxy]-phenyl}-2-methyl-2-phenoxy-propionic acid (11 g, 95%) was collected.

Workup

  1. customAfter most of the solve was removed in vacuo
  2. customthe white product was precipitated
  3. filtrationfiltered through celite, rac-3-{4-[2-Amino-6-(4-benzyl-piperazin-1-yl)-pyrimidin-4-yloxy]-phenyl}-2-methyl-2-phenoxy-propionic acid (11 g, 95%)
  4. customwas collected

Sources & evidence

ORD record
ord-6e764f57a3774bb88284bc2f29118be0
Source dataset
uspto-grants-2013_08
Patent number
US08513233B2

Reaction notes

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