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

HRID 394749노트

반응식

HRID 394749 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-155e81d1265b48bba93adec182005982
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602863B1

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