Water → HCID 86700702, compound

HRID 2408361Notes

Reaction equation

HRID 2408361 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[NH:9][CH2:8][C:7]3([CH2:11][CH2:10]3)[CH2:6][N:5]2[C:12](=[O:14])[CH:13]=1.[C:15](=O)([O-])[O-].[Cs+].[Cs+].O.[C:22]([O:25][CH2:26][CH3:27])(=O)[CH3:23]>CC#N>[Cl:1][C:2]1[N:3]=[C:4]2[N:9]([CH2:27][CH2:26][O:25][CH:22]([CH3:23])[CH3:15])[CH2:8][C:7]3([CH2:10][CH2:11]3)[CH2:6][N:5]2[C:12](=[O:14])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 136344294HCID 136344294, compound

Product 1

HCID 86700702HCID 86700702, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

0.1 g of 8′-chloro-1′,2′-dihydro-6′H-spiro[cyclopropane-1,3′-pyrimido[1,2-a]-pyrimidin]-6′-one are suspended in 10 mL of CH3CN, 0.2 g of cesium carbonate and 0.17 g of 2,2-isopropoxyethyl methanesulfonate are added. The mixture is heated to 65° C. for 72 h. Water, ethyl acetate are added and then after decantation, the organic phase is dried with magnesium sulfate and then evaporated. The crude is purified by flash chromatography on silica gel SiO2 (CH2Cl2/MeOH, 99/1). 0.1 g (yield=71%) of 8′-chloro-1′-(2-isopropoxyethyl)-1′,2′-dihydro-6′H-spiro[cyclopropane-1,3′-pyrimido[1,2-a]pyrimidin]-6′-one are obtained as a white powder including the following characteristics:

Workup

  1. dry with materialafter decantation, the organic phase is dried with magnesium sulfate
  2. customevaporated
  3. customThe crude is purified by flash chromatography on silica gel SiO2 (CH2Cl2/MeOH, 99/1)

Sources & evidence

ORD record
ord-15b6bc391a684445ad0082de6d925811
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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