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

HRID 1905898Notes

Reaction equation

HRID 1905898 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:24]=O)[C:21]([O-])=[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:24]=2)[CH:15]=[N:16][C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 202133063-(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 boiled under reflux for 0.75 hours. 3-(5,6-Dimethyl-3-pyridyl)-2-formylpropionate (14.3 g) was added and the mixture was boiled under reflux for 40 hours and evaporated to dryness. Water (40 ml) was added to the residue and the mixture was extracted with chloroform (discarded). The aqueous phase was adjusted to pH 6 with hydrochloric acid and the solid which separated out was filtered off and recrystallised from dimethylformamide-ethanol to give 5-(5,6-dimethyl-3-pyridylmethyl)-2-nitroamino-4-pyrimidone m.p. 212°-213°.

Workup

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

Sources & evidence

ORD record
ord-0b8d3ca746074b28bf274962a1465018
Source dataset
uspto-grants-1987_03
Patent number
US04649141

Reaction notes

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