Dichloromethane methanol acetic acid water → HCID 22125101, compound

HRID 1858232Notes

Reaction equation

HRID 1858232 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=O.ClCCl.[CH3:28][OH:29].[C:30](O)(=O)[CH3:31].[OH2:34]>>[CH2:12]([N:11]([CH2:30][CH3:31])[CH2:10][CH2:28][O:29][C:6]1[CH:7]=[CH:2][C:3]([NH:9][C:14]2[N:13]=[C:12]3[N:11]([CH3:23])[C:10](=[O:34])[N:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[CH2:18][C:17]3=[CH:16][N:15]=2)=[CH:4][CH:5]=1)[CH3:17]

Participants

3

Reactant 2

HCID 18914200Dichloromethane methanol acetic acid waterHCID 22125047HCID 22125047, compound

Product 1

HCID 22125101HCID 22125101, compoundYield 11%

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.56 mmol) of 3-(2,6-difluorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 400 mg (1.9 mmol) of 4-[1288 2-(diethylamino)ethoxy]aniline was heated at 180° C. for 30 minutes and then cooled. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined and evaporated and the residue was 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 to give 30 mg (11%) of 7-[4-[2-(diethylamino)ethoxy]anilino]-3-(2,6-difluorophenyl)-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as an orange colored solid. [Mass spectrum (ESI) MH+ =483].

Workup

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then dissolved in 40 ml of dichloromethane
  6. washwashed with 40 ml of saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-dc69eea1eec740d4b944d4e14ec7f3c2
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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