Thionyl Chloride → 4-Chloro-6-fluoropyrido[3,4-D]pyrimidine

HRID 394749ノート

反応式

HRID 394749 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 106790414-Chloro-6-fluoropyrido[3,4-D]pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-155e81d1265b48bba93adec182005982
出典データセット
uspto-grants-2003_08
特許番号
US06602863B1

反応ノート

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