Sodium Hydroxide → N-[4-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid

HRID 371469Notes

Reaction equation

HRID 371469 reaction equation
C([O:3][C:4](=[O:39])[C@H:5]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])[NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:21]([NH2:30])=[N:22][C:23]([NH2:29])=[N:24][C:25]=3[CH2:26][CH2:27][CH3:28])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)C.[OH-].[Na+]>CO.[OH-].[Na+]>[NH2:29][C:23]1[N:22]=[C:21]([NH2:30])[C:20]([N:17]2[CH2:16][CH2:15][N:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:39])=[O:3])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])=[CH:13][CH:12]=3)[CH2:19][CH2:18]2)=[C:25]([CH2:26][CH2:27][CH3:28])[N:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13478344N-[4-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid, diethyl ester

Product 1

HCID 13478342N-[4-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acidYield 75%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.3 g (2.47 mmole) of N-[4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]-benzoyl]-L-glutamic acid diethyl ester and 0.4 g (4.94 mmole) of a 50% aqueous sodium hydroxide solution in 300 ml of methanol was stirred at room temperature for four hours. One drop of 50% sodium hydroxide solution was added and the reaction mixture became a clear solution. Methanol was removed in vacuo below 23° C. The residue was dissolved in 200 ml of ice water and filtered. The filtrate was acidified with citric acid to pH 6. The precipitate was collected, washed with water, and triturated with boiling ethanol. After drying in vacuo at 78° C. for 16 hours, 0.9 g of the product was obtained as white powder, mp 280°-284° C.

Workup

  1. customMethanol was removed in vacuo below 23° C
  2. dissolutionThe residue was dissolved in 200 ml of ice water
  3. filtrationfiltered
  4. customThe precipitate was collected
  5. washwashed with water
  6. customtriturated with boiling ethanol
  7. customAfter drying in vacuo at 78° C. for 16 hours

Sources & evidence

ORD record
ord-a6229bea2d884774a6f97f2380775bba
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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