Ammonia → 4-Chloro-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

HRID 2189064ノート

反応式

HRID 2189064 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:17][C:11]2[N:12]=[CH:13][NH:14][C:15](=O)[C:10]=2[C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.P(Cl)(Cl)([Cl:28])=O.O.N>S1(CCCC1)(=O)=O>[Cl:28][C:15]1[C:10]2[C:9]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[O:17][C:11]=2[N:12]=[CH:13][N:14]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 962WaterHCID 24813Phosphorus oxychlorideHCID 580168816-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 580168704-Chloro-6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidine

試薬・触媒・溶媒 1

HCID 31347Sulfolane溶媒

実験手順

Stir a mixture of 20 g (0.06 mol) 6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one in 78 ml sulpholane and 11 ml (18 g, 0.12 mol) phosphoryl chloride for 1 h at 120° C. After cooling to room temperature, add the reaction solution dropwise to a mixture of 1000 ml water and 100 ml 25% aqueous ammonia solution, stirring vigorously and cooling with ice. Filter off the solid that is precipitated at 10° C. and wash several times with water. Dissolve the solid in 700 ml ethyl acetate again and wash the solution twice with 500 ml water each time. Dry the organic phase over sodium sulphate, filter, and concentrate the filtrate by vacuum evaporation. Mix the residue with 60 ml diisopropyl ether, filter, and dry under vacuum. 18 g (81% of theor.) of the title compound is obtained.

後処理

  1. additionadd the reaction solution
  2. stirringstirring vigorously
  3. temperaturecooling with ice
  4. filtrationFilter off the solid
  5. customthat is precipitated at 10° C.
  6. washwash several times with water
  7. dissolutionDissolve the solid in 700 ml ethyl acetate again
  8. washwash the solution twice with 500 ml water each time
  9. dry with materialDry the organic phase over sodium sulphate
  10. filtrationfilter
  11. concentrationconcentrate the filtrate
  12. customby vacuum evaporation
  13. additionMix the residue with 60 ml diisopropyl ether
  14. filtrationfilter
  15. customdry under vacuum

出典と根拠

ORDレコード
ord-3c733f054f2d4cdfa637392fb3534782
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

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