Hydrazine hydrate (1:1) → HCID 22125036, compound

HRID 1858258Notes

Reaction equation

HRID 1858258 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][CH2:37][N:38]4C(=O)C5=CC=CC=C5C4=O)[CH:31]=3)[C:15](=[O:29])[N:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=3[Cl:28])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:38][CH2:37][CH2:36][C:32]1[CH:31]=[C:30]([N:14]2[C:12]3=[N:13][C:8]([NH:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[N:9][CH:10]=[C:11]3[CH2:17][N:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=3[Cl:28])[C:15]2=[O:29])[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22125141HCID 22125141, compound

Product 1

HCID 22125036HCID 22125036, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 155 mg (0.23 mmol) of 7-anilino-3-(2-chloro-4-trifluoromethylphenyl)-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one in 20 ml of ethanol was treated with 0.3 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 40 ml of dichloromethane, washed with 40 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. Trituration of the residue with hexane followed by filtration afforded 40 mg (32%) of 1-[3-(2-aminoethyl)phenyl]-7-anilino-3-(2-chloro-4-trifluoromethylphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 102° C.

Workup

  1. customAfter 18 hours the mixture was evaporated
  2. customthe product purified by column chromatography on silica gel
  3. washfor the elution
  4. customevaporated
  5. customthe residue evaporated with toluene
  6. dissolutionThe residue was then dissolved in 40 ml of dichloromethane
  7. washwashed with 40 ml of saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. filtrationTrituration of the residue with hexane followed by filtration

Sources & evidence

ORD record
ord-85712064a406400597f3c87c8c2f7847
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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