Sodium Methoxide → 5-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidone

HRID 1248310Notes

Reaction equation

HRID 1248310 reaction equation
[N+:1]([NH:4][C:5]([NH2:7])=[NH:6])([O-:3])=[O:2].C[O-].[Na+].[CH3:11][C:12]1[CH:13]=[C:14]([CH2:19][CH:20]([CH:26]=O)[C:21](OCC)=[O:22])[CH:15]=[N:16][C:17]=1[CH3:18]>CO>[CH3:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]2[C:21](=[O:22])[NH:6][C:5]([NH:4][N+:1]([O-:3])=[O:2])=[N:7][CH:26]=2)[CH:15]=[N:16][C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12783847Ethyl 3-(5,6-dimethyl-3-pyridyl)-2-formylpropionateHCID 86287517Nitroguanidine

Product 1

HCID 127838315-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nitroguanidine (6.05 g) was added to a solution of sodium methoxide (prepared from 1.45 g sodium) in dry methanol (65 ml) and the mixture was heated under reflux for 0.75 hours. Ethyl 3-(5,6-dimethyl-3-pyridyl)-2-formylpropionate (14.3 g) was added and the mixture was heated under reflux for 40 hours and evaporated to dryness. Water (40 ml) was added to the residue and the mixture was extracted with chloroform. The aqueous phase was adjusted to pH 6 with hydrochloric acid and the solid which separated was filtered off and recrystallised from dimethylformamideethanol to give 5-(5,6-dimethyl-3-pyridylmethyl)-2-nitroamino-4-pyrimidone, m.p. 212°-3°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 0.75 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 40 hours
  5. customevaporated to dryness
  6. additionWater (40 ml) was added to the residue
  7. extractionthe mixture was extracted with chloroform
  8. customthe solid which separated
  9. filtrationwas filtered off
  10. customrecrystallised from dimethylformamideethanol

Sources & evidence

ORD record
ord-50d5d9933cde4594984dad6327e4ff6d
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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