Diethyl (ethoxymethylene)malonate → HCID 178450108, compound

HRID 2351841Notes

Reaction equation

HRID 2351841 reaction equation
Cl.[CH2:2]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[NH:12])=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.C[O-].[Na+].CO.[Na]>CO>[CH2:24]([O:23][C:21]([C:20]1[C:19]([OH:18])=[N:12][C:11]([C:10]2[CH:14]=[CH:15][C:7]([O:6][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[N:13][CH:26]=1)=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 3015453Benzamidine, p-butoxy-, monohydrochlorideHCID 5360545SodiumHCID 23694274Sodium methanolate methanol

Product 1

HCID 178450108HCID 178450108, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Butyloxybenzamidine hydrochloride (II) (22.9 g, 0.1 mol) and diethyl ethoxymethylenemalonate (III) (23.8 g, 0.1 mol) were suspended in methanol (100 ml), followed by agitating the suspension while keeping it at 10° C., dropwise adding a sodium methoxide-methanol solution, separately prepared by reacting sodium (2.5 g, 0.11 mol) with methanol (200 ml), then agitating the mixture for 2.5 hours, distilling off methanol under reduced pressure, gradually adding 6N-hydrochloric acid till the solution reached a pH of 4, filtering the resulting white precipitate, washing the precipitate with a small quantity of methanol and drying the precipitate to obtain ethyl-2-(4-butyloxyphenyl)-4-hydroxy-5-pyrimidinecarboxylate (IV) 21.9 g) (yield: 69% based on compound (II)).

Workup

  1. customat 10° C.
  2. customseparately prepared
  3. stirringagitating the mixture for 2.5 hours
  4. distillationdistilling off methanol under reduced pressure
  5. additiongradually adding 6N-hydrochloric acid till the solution
  6. filtrationfiltering the resulting white precipitate
  7. washwashing the precipitate with a small quantity of methanol
  8. customdrying the precipitate

Sources & evidence

ORD record
ord-d5aadeb06f51494f9b1057238aa19591
Source dataset
uspto-grants-1989_10
Patent number
US04874546

Reaction notes

Loading…