Dimethylformamide → N'-(7-Chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine

HRID 3412Notes

Reaction equation

HRID 3412 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](O)=[N:8][C:6]=2[N:7]=1.ClCCl.S(Cl)([Cl:26])=O.[CH3:28][N:29]([CH3:32])[CH:30]=O>>[Cl:26][C:9]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:11][C:5]2[CH:4]=[N:3][C:2]([N:1]=[CH:28][N:29]([CH3:32])[CH3:30])=[N:7][C:6]=2[N:8]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 1784184612-Amino-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-7-ol

Product 1

HCID 53718994N'-(7-Chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine

Procedure

To a mixture of 67.0 g of 2-amino-6-(4-methoxy-phenyl)-pyrido[2,3-d]pyrimidin-7-ol from Example 10, 1 L of dichloromethane, and 155 mL of dimethylformamide was added dropwise with cooling 72 mL of thionyl chloride keeping the temperature below 15° C. The suspension was heated to reflux with stirring for 6 hours. The reaction mixture was filtered and the filtrate evaporated in vacuo maintaining the temperature below 60° C. The resulting residue was dissolved in ice water and aqueous sodium hydroxide added with ice. The product was taken up in chloroform, washed with water, dried over anhydrous potassium carbonate, and evaporated. The residue was slurried with acetonitrile and the insoluble product collected by filtration to afford 31 g of the title compound N'-(7-chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine. The product was used in the next step without further purification.

Workup

  1. additionwas added dropwise
  2. temperatureThe suspension was heated
  3. temperatureto reflux
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated in vacuo
  6. temperaturemaintaining the temperature below 60° C
  7. dissolutionThe resulting residue was dissolved in ice water
  8. additionaqueous sodium hydroxide added with ice
  9. washwashed with water
  10. dry with materialdried over anhydrous potassium carbonate
  11. customevaporated
  12. filtrationthe insoluble product collected by filtration

Sources & evidence

ORD record
ord-e018a58eae26447a85248e2d7c5e33b2
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Reaction notes

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