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

HRID 1698962Notes

Reaction equation

HRID 1698962 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-d3215b4d576744c3bd85a1cf2c9e01a8
Source dataset
uspto-grants-2002_02
Patent number
US06344459B1

Reaction notes

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