Hydrochloric Acid → N-(3-bromophenyl)pyrido[3,2-d]pyrimidin-4-amine

HRID 2287666Notes

Reaction equation

HRID 2287666 reaction equation
Cl[C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].Cl>CC(O)C>[Br:12][C:13]1[CH:14]=[C:15]([NH:16][C:2]2[C:3]3[N:11]=[CH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 115623-BromoanilineHCID 131016394-Chloropyrido(3,2-d)pyrimidine

Product 1

HCID 5328273N-(3-bromophenyl)pyrido[3,2-d]pyrimidin-4-amineYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Reaction of 4-chloropyrido[3,2-d]pyrimidine (prepared as described in a previous experimental) with 3-bromoaniline in propan-2-ol containing a trace of conc. HCl at 50° C. for 30 min, followed by chromatography of the product on silica gel, gives 4-(3-bromophenyl)aminopyrido[3,2-d]pyrimidine (87% yield). 1H NMR (CDCl3) δ 9.19 (1H, brs), 8.83 (1H, s), 8.80 (1H, dd, J=4.3, 1.5 Hz), 8.29 (1H, brs), 8.19 (1H, dd, J=8.5, 1.5 Hz), 7.83 (1H, m), 7.76 (1H, dd, J=8.5, 4.3 Hz), 7.29-7.27 (2H, m).

Workup

  1. customprepared
  2. customat 50° C.
  3. customfor 30 min

Sources & evidence

ORD record
ord-3d3e74d8408a4c36bf98d65daffc220f
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

Loading…