Iodoethane → 6-ethyl-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one

HRID 333415Notes

Reaction equation

HRID 333415 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[CH2:5][CH2:4][NH:3]1.[H-].[Na+].I[CH2:14][CH3:15]>CN(C=O)C>[CH2:14]([N:3]1[CH2:4][CH2:5][C:6]2=[CH:10][N:9]=[CH:8][N:7]2[C:2]1=[O:1])[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 14875185H,6H,7H,8H-imidazo(1,5-c)pyrimidin-5-one

Product 1

HCID 126472846-ethyl-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 500 mg (3.6 mmol) of 5,6,7,8-tetrahydro-5-oxoimidazo[1,5-c]pyrimidine dissolved in 5 mL of DMF are added cautiously at room temperature 173 mg (4.32 mmol) of sodium hydride. The reaction medium is stirred for 1 hour at room temperature, and 0.35 mL (4.32 mmol) of iodoethane is then added dropwise. The reaction medium is stirred for 2 hours at room temperature and the solvents are then evaporated off. The residue is treated with 1N NaHCO3 solution and extracted with chloroform. The combined organic phases are dried with MgSO4, filtered and evaporated. The oil obtained is used directly in the following step.

Workup

  1. stirringThe reaction medium is stirred for 2 hours at room temperature
  2. customthe solvents are then evaporated off
  3. additionThe residue is treated with 1N NaHCO3 solution
  4. extractionextracted with chloroform
  5. dry with materialThe combined organic phases are dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe oil obtained

Sources & evidence

ORD record
ord-b9fc3996d22b4207a971a1dc312ba64b
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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