Water → HCID 86592158, compound

HRID 230211Notes

Reaction equation

HRID 230211 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[NH:17][CH2:16][CH2:15][CH2:14][N:10]3[C:11](=[O:13])[CH:12]=2)=[CH:3][CH:2]=1.[H-].[Na+].CS([O:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])(=O)=O.[OH2:35]>CN(C)C=O>[C:28]([OH:33])(=[O:13])/[CH:27]=[CH:26]\[C:25]([OH:24])=[O:35].[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][CH2:25][N:17]1[C:9]2=[N:8][C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:12][C:11](=[O:13])[N:10]2[CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21887279HCID 21887279, compoundHCID 135830901HCID 135830901, compound

Product 1

HCID 86592158HCID 86592158, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 0.25 g (1.09 mmol) of 2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in 3 ml of anhydrous dimethylformamide was treated with 57 mg (1.42 mmol) of sodium hydride (60% suspension in mineral oil) and the resulting mixture was heated at 70° C. for 30 min. 0.327 g (1.42 mmol) of 1-[2-(methylsulfonyloxy)ethyl]-2-methoxybenzene (prepared according to J. Med. Chem. 1983, 26(1), 42) was added and the reaction mixture was heated at 130° C. during 1 h. The cooled solution was treated with water and extracted with ethyl acetate. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with dichloromethane/methanol in the proportions 100/0 to 95/5. The 0.338 g of pure product obtained in the form of free base was dissolved in hot ethanol and treated with 1 equivalent of (Z)-but-2-enedioïc acid. The cooled solution was filtered to afford 0.325 g (62%) of white solid. Mp: 157-160° C.

Workup

  1. temperaturethe reaction mixture was heated at 130° C. during 1 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with dichloromethane/methanol in the proportions 100/0 to 95/5

Sources & evidence

ORD record
ord-34c30d98f255497ea5a09abc6aea80f8
Source dataset
uspto-grants-2009_07
Patent number
US07566720B2

Reaction notes

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