Sodium Methoxide → 2-Nitroamino-5-(1-naphthylmethyl)-4-pyrimidone

HRID 1248316Notes

Reaction equation

HRID 1248316 reaction equation
[N+:1]([NH:4][C:5]([NH2:7])=[NH:6])([O-:3])=[O:2].C[O-].[Na+].C([O:13][C:14](=O)[CH:15]([CH:27]=O)[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)C>CO>[N+:1]([NH:4][C:5]1[NH:7][C:14](=[O:13])[C:15]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:27][N:6]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 19592256Ethyl 2-formyl-3-(1-naphthyl)propionateHCID 86287517Nitroguanidine

Product 1

HCID 202792872-Nitroamino-5-(1-naphthylmethyl)-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Nitroguanidine (9.10 g) was added to a solution of sodium methoxide (from 2.22 g sodium) in methanol (100 ml) and the mixture was heated under reflux for 45 minutes, ethyl-2-formyl-3-(1-naphthyl)propionate (16.05 g) was added and the mixture was heated under reflux for 20 hours and evaporated to dryness. The residue was poured into water and the mixture was extracted with chloroform and the pH of the residual aqueous phase was adjusted to 4 with acetic acid. The solid which precipitated was recrystallised from acetic acid to give 2-nitroamino-5-(1-naphthylmethyl)-4-pyrimidone, m.p. 226°-7°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 20 hours
  5. customevaporated to dryness
  6. additionThe residue was poured into water
  7. extractionthe mixture was extracted with chloroform
  8. customThe solid which precipitated
  9. customwas recrystallised from acetic acid

Sources & evidence

ORD record
ord-5b6ea99f38c44a07b62db1af926e31eb
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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