Sodium Chloride → HCID 12052722, compound

HRID 505342Notes

Reaction equation

HRID 505342 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][NH:12][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1.[H-].[Na+].[CH2:21](Br)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].[Cl-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][N:12]([CH2:21][C:22](=[O:23])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 136353684HCID 136353684, compound

Product 1

HCID 12052722HCID 12052722, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution containing 0.608 g (2.5 mmol) of 3-methyl-2-(pyrimidin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one in anhydrous dimethylformamide was treated with 0.11 g (2.5 mmol) of sodium hydride (60% suspension in mineral oil) and the mixture warmed to 40° C. during 1 h. 0.497 g (2.5 mmol) of phenacyl bromide dissolved in 5 ml of dimethylformamide was added dropwise and the resulting solution stirred at room temperature for 3 h. The reaction mixture was treated with a saturated aqueous solution of sodium chloride and then extracted with ethyl acetate. The organic extracts were dried and evaporated to give a crude product, which was purified by chromatography on silica gel eluting with dichloromethane/methanol/ammonia in the proportions 100/0/0 to 98/2/0.2. A pure product was obtained which was triturated in diethylether to give 0.309 g (34%) of yellow solid. Mp.: 184-185° C.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts were dried
  4. customevaporated
  5. customto give a crude product, which
  6. customwas purified by chromatography on silica gel eluting with dichloromethane/methanol/ammonia in the proportions 100/0/0 to 98/2/0.2
  7. customA pure product was obtained which
  8. customwas triturated in diethylether

Sources & evidence

ORD record
ord-7cefc7013dbf48d8baf5259158112de1
Source dataset
uspto-grants-2010_08
Patent number
US07781440B2

Reaction notes

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