4-Aminophenol → 4-Anilino-2-(4-hydroxyanilino)pyrimidine

HRID 347756Notes

Reaction equation

[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1>C(O)CCC.Cl>[NH:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([OH:15])=[CH:17][CH:18]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Anilino-2-chloropyrimidine (Reference Example A-9, 0.921 g, 4.48 mmol) was dissolved in butanol (6 ml) and treated with 4-hydroxyaniline (0.489 g, 4.48 mmol) and conc. HCl (9 drops). The reaction was heated to 80° C. for 4 hours. The solvent was removed by evaporation at reduced pressure to give the title product as a solid which was used without further purification (1.4 g) NMR (300 MHz): 6.43 (d, 1H), 6.68 (d, 2H) 7.14 (t, 1H), 7.25 (m, 4H), 7.64 (m, 2H), 7.88 (s, 1H) 9.53 (brs, 1H), 10.27 (brs, 1H). 10.88 (brs, 1H); m/z: (ES−) 279 (MH+).

Workup

customThe solvent was removed by evaporation at reduced pressure

Sources & evidence

ORD record: ord-69cd0522e9c747d49854236b220b9da7
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176212B2

Reaction notes

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