Hydrazine hydrate (1:1) → HCID 22125163, compound

HRID 1858288Notes

Reaction equation

HRID 1858288 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][N:33]4C(=O)C5=CC=CC=C5C4=O)=[CH:28][CH:27]=3)[C:15](=[O:25])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[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>[NH2:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([N:14]2[C:12]3=[N:13][C:8]([NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][CH:10]=[C:11]3[CH2:17][N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Br:24])[C:15]2=[O:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22124998HCID 22124998, compound

Product 1

HCID 22125163HCID 22125163, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 160 mg (0.253 mmol) of 7-anilino-3-(2-bromophenyl)-3,4-dihydro-1-[4-(phthalimidomethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.5 ml of hydrazine hydrate in 5 ml of ethanol was stirred at room temperature under an atmosphere of nitrogen for 4 hours. The reaction mixture was evaporated and the residue purified by flash chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) as the eluent. Product containing fractions were combined and evaporated and the residue re-evaporated with toluene. The residue was then dissolved in 20 ml of dichloromethane, washed with saturated aqueous sodium bicarbonate (20 ml), dried over magnesium sulfate, filtered and evaporated to give 55 mg (43%) of 1-[4-(aminomethyl)phenyl]-7-anilino-3-(2-bromophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 133-136° C. [Mass spectrum (ESI) MH+ =501].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by flash chromatography on silica gel
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe residue re-evaporated with toluene
  6. dissolutionThe residue was then dissolved in 20 ml of dichloromethane
  7. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b3517f28aba2465083a920b6a9da4f2e
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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