Lithium hydride → HCID 20096998, compound

HRID 1769598Notes

Reaction equation

HRID 1769598 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:8][O:9][N+:10]=2[O-:11])[N:5]=[CH:6][N:7]=1.[H-].[Li+].Cl[CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[O:17]>C1COCC1>[CH3:19][N:18]([C:16]([CH2:15][N:7]1[C:2](=[O:1])[C:3]2=[N+:10]([O-:11])[O:9][N:8]=[C:4]2[N:5]=[CH:6]1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 178526302HCID 178526302, compound

Product 1

HCID 20096998HCID 20096998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.6 g (30 mmol) of 7-hydroxy-[1,2,5]oxadiazolo[3,4-d]pyrimidine-1-oxide and 0.28 g (35 mmol) of lithium hydride are heated at 50° C. for 30 minutes in 65 ml of THF. A solution of 4.6 g (38 mmol) of 2-chloro-N,N-dimethylacetamide in 10 ml of THF is then added dropwise and the mixture is heated under reflux for 4 hours. The solvent is completely stripped off in a rotary evaporator and the residue is stirred with 30 ml of water for 2 hours. The precipitate is filtered off with suction and recrystallised from THF, and 2.4 g (33%) of 6-(N,N-dimethylaminocarbonylmethyl)[1,2,5]oxadiazolo[3,4-d]pyrimidine-7(6H)-one-1-oxide are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent is completely stripped off in a rotary evaporator
  4. filtrationThe precipitate is filtered off with suction
  5. customrecrystallised from THF, and 2.4 g (33%) of 6-(N,N-dimethylaminocarbonylmethyl)[1,2,5]oxadiazolo[3,4-d]pyrimidine-7(6H)-one-1-oxide
  6. customare obtained

Sources & evidence

ORD record
ord-56e4d1b1551e488b9cb55439420f886f
Source dataset
uspto-grants-1995_01
Patent number
US05382585

Reaction notes

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