Water → HCID 67982936, compound

HRID 2408355Notes

Reaction equation

HRID 2408355 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[NH:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30])(=O)=O.O>CC#N.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:12]([CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30])[C:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 184650452-Isopropoxyethyl MethanesulfonateHCID 136344289HCID 136344289, compound

Product 1

HCID 67982936HCID 67982936, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

0.2 g of 2-chloro-8,8-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are suspended in 7 mL of CH3CN, 0.61 g of cesium carbonate and 0.34 g of 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). 0.19 g (yield=67%) of 2-chloro-9-(2-isopropoxyethyl)-8,8-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-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-94319d2ed44543afb837e27df35857d9
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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