3-Bromoaniline → N-(3-bromophenyl)-7H-purin-6-amine

HRID 1059645Notes

Reaction equation

HRID 1059645 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>Cl.C(O)(C)C>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[NH:4][CH:5]=[N:6]3)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 53592776-Chloropurine

Product 1

HCID 9814520N-(3-bromophenyl)-7H-purin-6-amineYield 102.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-chloropurine (1.0 g, 6.47 mmol), 3-bromoaniline (0.78 mL, 7.12 mmol), and conc HCl (4 drops) in isopropanol (10 mL) is stirred at 80° C. for 5 h. Upon cooling, it precipitates. The solid is filtered and washed with isopropanol and air dried to yield N6-(3-bromophenyl)adenine (1.93 g, 91%) as a light yellow solid. 1H NMR (DMSO) δ 11.38 (1H, s), 8.78 (1H, s), 8.75 (1H, s), 7.90 (1H, d, J=8.0 Hz), 7.38-7.34 (2H, m).

Workup

  1. temperatureUpon cooling
  2. customit precipitates
  3. filtrationThe solid is filtered
  4. washwashed with isopropanol and air
  5. customdried

Sources & evidence

ORD record
ord-0488cb33e009460d8d4e60dd7b96d9a1
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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