Dimethylformamide dimethyl acetal → 2,4,7-Tri(dimethylaminomethyleneamino)-6-(2-chlorophenyl)pteridine

HRID 1734148Notes

Reaction equation

HRID 1734148 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][C:6]([NH2:20])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:8]=2)[N:3]=1.CO[CH:23](OC)[N:24]([CH3:26])[CH3:25]>>[CH3:23][N:24]([CH:26]=[N:1][C:2]1[N:11]=[C:10]([N:12]=[CH:23][N:24]([CH3:26])[CH3:25])[C:9]2[C:4](=[N:5][C:6]([N:20]=[CH:23][N:24]([CH3:26])[CH3:25])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N:8]=2)[N:3]=1)[CH3:25]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 152789352,4,7-Triamino-6-(2-chlorophenyl)pteridine

Product 1

HCID 545557082,4,7-Tri(dimethylaminomethyleneamino)-6-(2-chlorophenyl)pteridine

Procedure

Under a nitrogen atmosphere, a stirred solution of 0.5 gram (0.002 mole) of 2,4,7-triamino-6-(2-chlorophenyl)pteridine (prepared in Example 2) in 50 mL of N,N-dimethylformamide dimethylacetal was heated at reflux for about 5 hours. After this time the reaction mixture was cooled in an ice-bath, and a solid was collected by filtration. The solid was washed with diethyl ether, yielding, when dried, 0.5 gram of 2,4,7-tri-(dimethylaminomethyleneamino)-6-(2-chlorophenyl)pteridine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 5 hours
  2. temperatureAfter this time the reaction mixture was cooled in an ice-bath
  3. filtrationa solid was collected by filtration
  4. washThe solid was washed with diethyl ether
  5. customyielding
  6. customwhen dried

Sources & evidence

ORD record
ord-343a4fc54a96462c81fcfccb1d45cf8d
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Reaction notes

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