m-Toluidine → HCID 15341440, compound

HRID 725850Notes

Reaction equation

HRID 725850 reaction equation
Cl[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.[CH3:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].C(N(CC)CC)C>O1CCOCC1>[CH3:14][C:15]1[CH:16]=[C:17]([NH:18][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:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 152952158-Chloro-2-(methylsulfanyl)pyrimido[5,4-d]pyrimidine

Product 1

HCID 15341440HCID 15341440, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.9 g of 4-chloro-6-methylthio-pyrimido[5,4-d]pyrimidine, 2.0 g of 3-methylaniline, 2.4 ml of triethylamine and 100 ml of dioxane are heated at 100° C. for 3 hours. After cooling, the reaction mixture is concentrated and partitioned between water and methylene chloride. The organic phase is separated off, dried and concentrated and the residue is purified by chromatography over a silica gel column (petroleum ether/ethyl acetate=2:1). The solid is triturated with diethyl ether, filtered off with suction and dried.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated
  3. custompartitioned between water and methylene chloride
  4. customThe organic phase is separated off
  5. customdried
  6. concentrationconcentrated
  7. customthe residue is purified by chromatography over a silica gel column (petroleum ether/ethyl acetate=2:1)
  8. customThe solid is triturated with diethyl ether
  9. filtrationfiltered off with suction
  10. customdried

Sources & evidence

ORD record
ord-259adcf414d642e6b7dfa222e3c883a3
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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