Hydrochloric Acid → N-benzyloxycarbonyl-4,6-diaminopyrimidine

HRID 2260561

Reaction equation

HRID 2260561 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.C(O)C>[CH2:12]([O:19][C:20]([N:3]1[C:2]([NH2:1])=[CH:7][C:6]([NH2:8])=[N:5][CH2:4]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 79608Pyrimidine-4,6-diamine

Product 1

HCID 18998616N-benzyloxycarbonyl-4,6-diaminopyrimidineYield 36.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4,6-diaminopyrimidine (4.7 g), ethanol (500 ml) and water (200 ml) was added 1N sodium hydroxide (13.25 ml) while cooling with ice water. After the dropwise addition of 1N hydrochloric acid (26.5 ml) thereto, benzyloxycarbonyl chloride (4.5 g) was dropwise added thereto. After being stirred at room temperature for 2 hours, the mixture was concentrated under reduced pressure to give crystals. The crystals were collected by filtration and recrystallized from chloroform:methanol=5:1 to give 2.4 g of N-benzyloxycarbonyl-4,6-diaminopyrimidine, melting point 194° C.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give crystals
  3. filtrationThe crystals were collected by filtration
  4. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-c1a138af9c1841a4a3c5349e166eb593
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Linked notes

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