Ammonium Hydroxide → 2,4-Diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazoline

HRID 363758Notes

Reaction equation

HRID 363758 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[O:21]C)[C:8]=2[Cl:13])[N:3]=1.B(Br)(Br)Br.[OH-].[NH4+]>C(Cl)Cl>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[OH:21])[C:8]=2[Cl:13])[N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 540726682,4-Diamino-5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline

Product 1

HCID 543690952,4-Diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazolineYield 8.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.8 grams (0.084 mole) of 2,4-diamino-5-chloro-6-(5-chloro-2-methoxyphenyl)quinazoline (prepared in Example 2) in 300 mL of methylene chloride was stirred, and 35 mL of 1.0M boron tribromide in methylene chloride was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 21 hours. Thin layer chromatographic analysis of the reaction mixture indicated that the reaction was not complete. The reaction mixture was heated at reflux for about 6 hours, then it was allowed to cool to ambient temperature where it was stirred for about 60 hours. After this time, the reaction mixture was poured into 500 mL of ice containing 100 mL of concentrated ammonium hydroxide. The mixture was filtered to collect a solid. The solid was washed with water and dried at 70° C. under reduced pressure, yielding 2.4 grams of 2,4-diamino-5-chloro-6-(5-chloro-2-hydroxyphenyl)quinazoline. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for about 6 hours
  4. temperatureto cool to ambient temperature where it
  5. stirringwas stirred for about 60 hours
  6. filtrationThe mixture was filtered
  7. customto collect a solid
  8. washThe solid was washed with water
  9. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-9811d61b809b425d97ebcd15891545a7
Source dataset
uspto-grants-1999_02
Patent number
US05874579

Reaction notes

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