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

HRID 1386137Notes

Reaction equation

HRID 1386137 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-94c779d8cec445aab24b487adeede315
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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