Acetonitrile → HCID 67982473, compound

HRID 2408347Notes

Reaction equation

HRID 2408347 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.CC#N.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH2:29][CH2:30][O:31][CH3:32])(=O)=O>C(OCC)(=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]2[N:12]([CH2:29][CH2:30][O:31][CH3:32])[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 6342AcetonitrileHCID 10796Cesium carbonateHCID 1462932-Methoxyethyl methanesulfonateHCID 136344289HCID 136344289, compound

Product 1

HCID 67982473HCID 67982473, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

0.19 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 de CH3CN, 0.58 g of cesium carbonate and 0.27 g of 2-methoxyethyl methanesulfonate are added. The mixture is heated to 65° C. for 36 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). 0.17 g (yield=50%) of 2-chloro-9-(2-methoxyethyl)-8,8-dimethyl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained as a brown powder including the following characteristics:

Workup

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

Sources & evidence

ORD record
ord-e758637ede6241099cc6d6811f68265d
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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