Water → 2,4-Diamino-6-[3,5-di(trifluoromethyl)phenyl]pteridine

HRID 440893Notes

Reaction equation

HRID 440893 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:4][N:3]=1.C(=O)(O)O.[NH2:28][C:29]([NH2:31])=[NH:30].O>CN(C)C(=O)C>[NH2:30][C:29]1[N:31]=[C:8]([NH2:9])[C:7]2[C:2](=[N:3][CH:4]=[C:5]([C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:22])([F:21])[F:23])[CH:11]=3)[N:6]=2)[N:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 286947Carbonic acid-guanidine (1:1)HCID 153352682-Amino-3-cyano-5-[3,5-di(trifluoromethyl)phenyl]pyrazine

Product 1

HCID 153352722,4-Diamino-6-[3,5-di(trifluoromethyl)phenyl]pteridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 1.0 gram (0.003 mole) of 2-amino-3-cyano-5-[3,5-di(trifluoromethyl)phenyl]pyrazine and 1.3 grams (0.007 mole) of guanidine carbonate in 10 mL of N,N-dimethylacetamide is heated at about 150° C. for 40 hours. After this time, the reaction mixture is poured into 50 mL of water. The resultant solid is collected by filtration and is then slurried in 25 mL of diethyl ether. The solid is again collected by filtration and is then recrystallized from ethanol, yielding 2,4-diamino-6-[3,5-di(trifluoromethyl)phenyl]pteridine.

Workup

  1. filtrationThe resultant solid is collected by filtration
  2. filtrationThe solid is again collected by filtration
  3. customis then recrystallized from ethanol

Sources & evidence

ORD record
ord-1a324f2f1d5e4766bbb0947202ee59a0
Source dataset
uspto-grants-1996_05
Patent number
US05521190

Reaction notes

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