Phosphorus oxychloride → 2-Chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33965

반응식

HRID 33965 반응식
O[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:3]=1.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:3]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178481601HCID 178481601, 화합물

생성물 1

HCID 221851932-Chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

반응 조건

온도
105 °C

실험 절차

A suspension of 2-hydroxy-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (10.0 g, 30.4 mmol) and phosphorous oxychloride (250 mL, 3 mol) was heated to 105° C. for 6 h to form a solution. Monitoring reaction by HPLC showed ˜90% conversion. The reaction solution was cooled and the solvent removed under reduced pressure. Foam residue was dissolved in 500 mL 5% ethanol/chloroform. The organic layer was washed with 100 mL water three times and once with 100 mL 5% NaHCO3. Organic dried over magnesium sulfate, then dried onto 30 g of silica. Final product purified on 400 g silica eluting with 0 to 2.5% methanol/dichloromethane to give a yellow solid. M+1=348.

후처리

  1. customto form a solution
  2. customMonitoring reaction by HPLC
  3. temperatureThe reaction solution was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionFoam residue was dissolved in 500 mL 5% ethanol/chloroform
  6. washThe organic layer was washed with 100 mL water three times and once with 100 mL 5% NaHCO3
  7. dry with materialOrganic dried over magnesium sulfate
  8. customdried onto 30 g of silica
  9. customFinal product purified on 400 g silica eluting with 0 to 2.5% methanol/dichloromethane
  10. customto give a yellow solid

출처 및 근거

ORD 기록
ord-5a48cb219acb4ecd8926f656b8e47788
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429594B2

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