HCID 15405282, compound → HCID 86753748, compound

HRID 363792Notes

Reaction equation

HRID 363792 reaction equation
N[C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=3)[C:8]=2C)[N:3]=1.[CH3:28]N(C=NC1N=C(N=CN(C)C)C2C(=CC=C(C3C=C(C(F)(F)F)C=C(C(F)(F)F)C=3)C=2C)N=1)C>COC(OC)N(C)C>[CH3:28][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[C:18]([C:20]([F:22])([F:21])[F:23])[CH:17]=[C:16]([C:24]([F:26])([F:25])[F:27])[CH:15]=3)[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 15405282HCID 15405282, compoundHCID 54246125HCID 54246125, compound

Product 1

HCID 86753748HCID 86753748, compound

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 1.0 gram (0.0026 mole) of 2,4-diamino-5-methyl-6-[3,5-di(trifluoromethyl)phenyl]quinazoline (Compound 63-prepared as in Example 1) in 20 mL of dimethylformamide dimethyl acetal was heated at 80° C. for about 18 hours. After this time, the reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was then triturated with petroleum ether, and the resulting solid was collected by filtration. The filter cake was washed with petroleum ether and dried, yielding about 1.1. grams of 2,4-di(dimethylaminomethyleneamino)-5-methyl-6-[3,5-di(trifluoromethyl)phenyl]quinazoline, mp 208°-210° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure to a residue
  3. customThe residue was then triturated with petroleum ether
  4. filtrationthe resulting solid was collected by filtration
  5. washThe filter cake was washed with petroleum ether
  6. customdried
  7. customyielding about 1.1

Sources & evidence

ORD record
ord-e22affd6f59f4409bd78de8174ab79ea
Source dataset
uspto-grants-1999_02
Patent number
US05874579

Reaction notes

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