p-Toluenesulfonic acid → HCID 21830556, compound

HRID 1600675Notes

Reaction equation

HRID 1600675 reaction equation
O[C:2]1[C:3]2[N:11]=[C:10]([S:12][CH3:13])[N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](C)(C)N[Si](C)(C)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[C:3]3[N:11]=[C:10]([S:12][CH3:13])[N:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 97083-Chloro-4-fluoroanilineHCID 13838HexamethyldisilazaneHCID 1785034026-methylsulfanyl-1H-pyrimido[5,4-d]pyrimidin-4-one

Product 1

HCID 21830556HCID 21830556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

148 g of 4-hydroxy-6-methylthiopyrimido[5,4-d]pyrimidine, 286 ml of hexamethyldisilazane, 333 g of 3-chloro-4-fluoroaniline and 15 g of p-toluenesulphonic acid are heated at 140° C. for 23 hours. The reaction mixture is cooled and, after addition of 4 1 of methanol, heated at 100° C. for one hour. The methanol is distilled off and the residue is triturated three times with diethyl ether and filtered off with suction.

Workup

  1. temperatureThe reaction mixture is cooled
  2. distillationThe methanol is distilled off
  3. customthe residue is triturated three times with diethyl ether
  4. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-f4435e0d26e84b399d3fcec5d9ede680
Source dataset
uspto-grants-1999_11
Patent number
US05977102

Reaction notes

Loading…