Hydrochloric Acid → 4-Anilino-5-bromo-2-(4-hydroxyanilino)pyrimidine

HRID 1759755Notes

Reaction equation

HRID 1759755 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl.[NH:10]([C:17]1[C:22]([Br:23])=[CH:21][N:20]=[C:19](Cl)[N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)CCC>[NH:10]([C:17]1[C:22]([Br:23])=[CH:21][N:20]=[C:19]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 114033895-bromo-2-chloro-N-phenylpyrimidin-4-amine

Product 1

HCID 220481234-Anilino-5-bromo-2-(4-hydroxyanilino)pyrimidineYield 32%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

4-Aminophenol (0.73 g, 7.8 mmol) and concentrated hydrochloric acid (1.30 ml, 7.1 mmol) were added to 4-anilino-5-bromo-2-chloropyrimidine (Method 1; 3.0 g, 7.1 mmol) in n-butanol (30 ml), and the mixture was heated at 100° C. for 12 hours. The solid which precipitated out on cooling was filtered off and washed with n-butanol and diethyl ether to give the product (0.80 g, 32%). MS (MH+): 357, 359.

Workup

  1. customThe solid which precipitated out
  2. temperatureon cooling
  3. filtrationwas filtered off
  4. washwashed with n-butanol and diethyl ether

Sources & evidence

ORD record
ord-7e3b4f59ce5142058f3caa293d495a99
Source dataset
uspto-grants-2005_01
Patent number
US06838464B2

Reaction notes

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