P-Anisidine → HCID 131722158, compound

HRID 1858270Notes

Reaction equation

HRID 1858270 reaction equation
BrC1C=CC=CC=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[N:10](C2C=CC=C(CCN3C(=O)C4=CC=CC=C4C3=O)C=2)[C:9]1=[O:41].[CH3:42][O:43][C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=1>Cl>[CH3:42][O:43][C:44]1[CH:50]=[CH:49][C:47]([NH:48][N:10]2[C:11]3=[N:12][CH:13]=[N:14][CH:15]=[C:16]3[CH2:17][NH:8][C:9]2=[O:41])=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 22125018HCID 22125018, compound

Product 1

HCID 131722158HCID 131722158, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 130 mg (0.31 mmol) of 3-(2-bromophenyl)-7-methanesulfonyl-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one from Example 50 was treated with 1 g (8 mmol) of 4-methoxyaniline. The mixture was heated to 120° C. for 2 hours. The mixture was cooled and treated with 30 ml of 2M aqueous hydrochloric acid. The suspended solid was filtered, washed with water and dried. The solid was dissolved in 20 ml of ethanol and treated with 0.2 ml of hydrazine hydrate. After 18 hours the mixture was evaporated and the product purified by column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined, evaporated and the residue evaporated with toluene. The residue was then dissolved in 50 ml of dichloromethane, washed with 50 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated to give 35 mg (31%) of 1-[3-(2-aminoethyl)phenyl]-3-(2-bromophenyl)-7-(4-methoxyanilino-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 132-133° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe suspended solid was filtered
  3. washwashed with water
  4. customdried
  5. dissolutionThe solid was dissolved in 20 ml of ethanol
  6. additiontreated with 0.2 ml of hydrazine hydrate
  7. customAfter 18 hours the mixture was evaporated
  8. customthe product purified by column chromatography on silica gel
  9. washfor the elution
  10. customevaporated
  11. customthe residue evaporated with toluene
  12. dissolutionThe residue was then dissolved in 50 ml of dichloromethane
  13. washwashed with 50 ml of saturated aqueous sodium bicarbonate solution
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. customevaporated

Sources & evidence

ORD record
ord-c3351e7d842d45219e5a134017fe5440
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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