Potassium Carbonate → 2,4-Diamino-6-(3,4-dichlorophenyl)-7-methylpteridine

HRID 1734146Notes

Reaction equation

HRID 1734146 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]=O)=[C:4]([NH2:11])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][C:27](=O)[CH3:28])[CH:22]=[CH:23][C:24]=1[Cl:25]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]2[C:4](=[N:11][C:27]([CH3:28])=[C:26]([C:21]3[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=3)[N:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 705045-Nitroso-2,4,6-pyrimidinetriamineHCID 810603',4'-Dichloropropiophenone

Product 1

HCID 152789342,4-Diamino-6-(3,4-dichlorophenyl)-7-methylpteridineYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.0 gram (0.007 mole) of 2,4,6-triamino-5-nitrosopyrimidine and 2.7 grams (0.020 mole) of potassium carbonate in 30 mL of N,N-dimethylformamide was heated to 95°-100° C., and 2.0 grams (0.010 mole) of (3,4-dichlorophenyl)acetone was added in one portion. Upon completion of addition, the reaction mixture was allowed to cool to ambient temperature, where it was allowed to stir for about 18 hours. After this time the reaction mixture was concentrated under reduced pressure. The residue was triturated with 250 mL of water, and the remaining solid was collected by filtration. The solid was further triturated with 50 mL of 20% methanol in methylene chloride. The remaining solid was collected by filtration, yielding 0.5 gram of 2,4-diamino-6-(3,4-dichlorophenyl)-7-methylpteridine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure
  3. customThe residue was triturated with 250 mL of water
  4. filtrationthe remaining solid was collected by filtration
  5. customThe solid was further triturated with 50 mL of 20% methanol in methylene chloride
  6. filtrationThe remaining solid was collected by filtration

Sources & evidence

ORD record
ord-fb230cfa2d2e4d3c8a4839a57e69a57d
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Reaction notes

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