4-Aminophenol → 4-(4-Hydroxyanilino)-6-chloropyrimidine

HRID 987548Notes

Reaction equation

HRID 987548 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C(O)C.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>C(N(CC)CC)C>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 702EthanolHCID 709434,6-Dichloropyrimidine

Product 1

HCID 180091284-(4-Hydroxyanilino)-6-chloropyrimidineYield 69.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 4,6-dichloropyrimidine (24.8 g), ethanol (250 ml) and triethylamine (51 ml) was added 4-aminophenol (18.2 g) and the solution was heated at reflux for 6 hours. After cooling the precipitate was collected, washed with DCM (100 ml) and recrystallized in acetonitrile to give the title compound (25.6 g, 69%) as crystals. NMR: 6.59 (1H, s), 6.73 (2H, d), 7.28 (2H, d), 8.33 (1H, s), 9.28 (1H, s), 9.52 (1H, s); m/z 222 (NH+).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling the precipitate
  4. customwas collected
  5. washwashed with DCM (100 ml)
  6. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-d5962015454f46a583da5de41423fa0f
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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