Sodium hydride → HCID 57407136, compound

HRID 2408356Notes

Reaction equation

HRID 2408356 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:18][N:6]2[C:7](=[O:17])[CH:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:10]=[C:5]2[NH:4][CH2:3]1.[H-].[Na+].CS(O[CH2:27][CH2:28][O:29][CH3:30])(=O)=O>CN(C=O)C>[CH3:30][O:29][CH2:28][CH2:27][N:4]1[C:5]2=[N:10][C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][C:7](=[O:17])[N:6]2[CH2:18][C:2]([CH3:19])([CH3:1])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1462932-Methoxyethyl methanesulfonateHCID 136344291HCID 136344291, compound

Product 1

HCID 57407136HCID 57407136, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.22 g of 7,7-dimethyl-2-(morpholin-4-yl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]-pyrimidin-4-one are solubilized in anhydrous DMF. 0.7 g of 60% NaH are added and stirred for 30 mins. 0.24 g of 2-methoxyethyl methanesulfonate are added and the mixture is heated with reflux for 3 h. After returning to RT, the mixture is poured into a water/ice/AcOEt mixture. The organic phase is decanted, washed with a solution saturated with NaCl and then dried with magnesium sulfate. The solvents are evaporated. The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 95/5). 0.1 g (yield=39%) of 9-(2-methoxyethyl)-7,7-dimethyl-2-(morpholin-4-yl)-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. temperaturethe mixture is heated
  2. temperaturewith reflux for 3 h
  3. customAfter returning to RT
  4. customThe organic phase is decanted
  5. washwashed with a solution saturated with NaCl
  6. dry with materialdried with magnesium sulfate
  7. customThe solvents are evaporated
  8. customThe crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 95/5)

Sources & evidence

ORD record
ord-213af15eb84449bf8329c82a4de5ab86
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

Loading…