Thionyl Chloride → 4-CHLORO-6-FLUOROPYRIDO[3,4-D]PYRIMIDINE

HRID 507471Notes

Reaction equation

HRID 507471 reaction equation
[F:1][C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[CH:3]=1.S(Cl)([Cl:15])=O>CN(C)C=O>[Cl:15][C:9]1[C:4]2[CH:3]=[C:2]([F:1])[N:12]=[CH:11][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354173706-fluoropyrido[3,4-d]pyrimidin-4-ol

Product 1

HCID 106790414-CHLORO-6-FLUOROPYRIDO[3,4-D]PYRIMIDINE

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A suspension of 6-fluoropyrido[3,4-d]pyrimidine-4(3H)-one (U.S. patent application Ser. No. 08/358,352, 1994) (1.65 g) in 50 mL thionyl chloride and several drops of dimethyl formamide was heated under reflux until a clear solution was obtained (20 minutes), and then for a further 30 minutes. The volatiles were removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with aqueous Na2CO3. The solvent was dried and removed to give crude 4-chloro-6-fluoropyrido[3,4-d]pyrimidine which was dissolved in 2-propanol (50 mL) containing 3-bromoaniline (2.1 g). The mixture was heated under reflux for 15 minutes to give a precipitate, which was redissolved by the addition of triethylamine. After the addition of water, the solution was concentrated and cooled to give 4-[(3-bromophenyl)amino]-6-fluoropyrido[3,4-d]-pyrimidine, (2.29 g), mp (MeOH) 219.5-221° C.

Workup

  1. temperatureunder reflux until a clear solution
  2. customwas obtained (20 minutes)
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with aqueous Na2CO3
  6. customThe solvent was dried
  7. customremoved

Sources & evidence

ORD record
ord-7949ece304524ae3800bb11bd41e52da
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

Loading…