Sodium Iodide → HCID 15233812, compound

HRID 1729025Notes

Reaction equation

HRID 1729025 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH3:18])[N:8]=1)=[O:6].Cl[C:31]1[N:36]=[C:35]([C:37]([NH2:39])=[O:38])[CH:34]=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[NH2:39][C:37]([C:35]1[CH:34]=[CH:33][N:32]=[C:31]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH3:18])[N:8]=2)=[O:6])[N:36]=1)=[O:38]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2470282-Chloropyrimidine-4-carboxamideHCID 54522065HCID 54522065, compound

Product 1

HCID 15233812HCID 15233812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3.0 g (7.45 mmol) of N-(2-aminoethyl)-2-[[3-[[2-(2-methoxyphenoxy) ethyl]methylamino]propyl]amino]-pyrimidine-4-carboxamide, 1.23 g (7.8 mmol) of 2-chloropyrimidine-4-carboxamide, 1.55 g (11.2 mmol) of potassiumcarbonate and 0.1 g of sodium iodide are introduced into 40 ml of N,N-dimethylformamide in a 0.25 l, three-necked, round-bottomed flask and the reaction mixture is heated at 60° C. for 15 h. The mixture is cooled to room temperature and the reaction product is poured onto 100 ml of water and extracted with ethyl acetate (3×100 ml). The organic phase is washed with water, dried over sodium sulphate, filtered and the solvents are evaporated under reduced pressure. After recrystallisation from ethyl acetate, 1.95 g of compound are obtained.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvents are evaporated under reduced pressure
  7. customAfter recrystallisation from ethyl acetate, 1.95 g of compound
  8. customare obtained

Sources & evidence

ORD record
ord-d0b566d4e50d46bbba745133b89476a9
Source dataset
uspto-grants-1994_07
Patent number
US05330985

Reaction notes

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