Sodium Methoxide → HCID 12783831, compound

HRID 224869Notes

Reaction equation

HRID 224869 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 20213306HCID 20213306, compoundHCID 86287517Nitroguanidine

Product 1

HCID 12783831HCID 12783831, compound

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°. (viii) A mixture of 2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamine (1.39 g), (5-(5,6-dimethyl-3-pyridylmethyl)-2-nitroamino-4-pyrimidone (1.51 g) and ethanol (25 ml) was boiled under reflux for 48 hours and evaporated to dryness. The residue was triturated with water (discarded) to leave 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-pyrimidone which was treated with ethanolic HCl and recrystallised three times from methanol/ethanol to give 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone trihydrochloride m.p. 221°-224°.

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-ad6eaaa2bb6541fb9db2e00f3419c8fd
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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