Aniline → Phenyl-pyrido[2,3-d]pyrimidin-4-yl-amine

HRID 1937392Notes

Reaction equation

HRID 1937392 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[CH:10][CH:9]=[N:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[NH4+]>O>[C:13]1([NH:12][C:2]2[C:3]3[CH:11]=[CH:10][CH:9]=[N:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 14923Ammonium HydroxideHCID 5690394-Chloropyrido[2,3-d]pyrimidine

Product 1

HCID 22460822Phenyl-pyrido[2,3-d]pyrimidin-4-yl-amineYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloropyrido [2,3-d]pyrimidine (0.15 g, 0.91 mmol) was carefully added to a solution of aniline (0.15 g, 1.61 mmol) in water (1.5 mL). The solution was heated for 0.5 h on a steam bath, cooled, and then basified with conc. ammonium hydroxide. The crude precipitate was collected by filtration and recrystallized from 95% ethanol to give yellow crystals (0.054 g, 27%). MP 258° C.; LC-MS: 223 (MH+).

Workup

  1. temperatureThe solution was heated for 0.5 h on a steam bath
  2. temperaturecooled
  3. filtrationThe crude precipitate was collected by filtration
  4. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-60685f475e5143c3a362fcc608eec26a
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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