Water → N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amine

HRID 2287671Notes

Reaction equation

HRID 2287671 reaction equation
Cl[C:2]1[C:3]2[N:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].O>CC(O)C.Cl>[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH:17][C:2]1[C:3]2[N:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 115623-BromoanilineHCID 106313224-Chloro-6-fluoropyrido[3,2-D]pyrimidine

Product 1

HCID 5328276N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-6-fluoropyrido[3,2-d]pyrimidine (0.20 g, 1.1 mmol) and 3-bromoaniline (0.12 mL, 2.18 mmol) in propan-2-ol (20 mL) containing conc. HCl (1 drop) is heated under reflux for 15 min, then cooled, poured into water and extracted with EtOAc. The extract is worked up, and the residue chromatographed on silica gel, eluting with EtOAc/petroleum ether (1:2)to give after removal of the solvent under reduced pressure 4-(3-bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (0.18 g, 52%). 1H NMR (CDCl3) δ 8.82 (1H, s), 8.65 (1H, brs), 8.31 (1H, t, J=7.4 Hz), 8.27 (1H, brs), 7.77 (1H, m) 7.41 (1H, dd, J=8.9, 2.2 Hz), 7.29 (2H, brs).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 min
  3. temperaturecooled
  4. extractionextracted with EtOAc
  5. customthe residue chromatographed on silica gel
  6. washeluting with EtOAc/petroleum ether (1:2)to
  7. customgive
  8. customafter removal of the solvent under reduced pressure 4-(3-bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (0.18 g, 52%)

Sources & evidence

ORD record
ord-229a26cf31584d9e91cda5e8b08539c1
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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