Dimethyl malonate → 4(3H)-Pyrimidinone, 6-hydroxy-2-[4-(trifluoromethyl)phenyl]-

HRID 1457744Notes

Reaction equation

HRID 1457744 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.C[O-].[K+].[C:18](OC)(=[O:24])[CH2:19][C:20](OC)=[O:21]>CO>[OH:24][C:18]1[N:10]=[C:8]([C:7]2[CH:11]=[CH:12][C:4]([C:3]([F:13])([F:14])[F:2])=[CH:5][CH:6]=2)[NH:9][C:20](=[O:21])[CH:19]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 125357914-(Trifluoromethyl)benzamidine HydrochlorideHCID 23664618Potassium methoxide

Product 1

HCID 154770924(3H)-Pyrimidinone, 6-hydroxy-2-[4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-Trifluormethylbenzamidine hydrochloride (22.4 g, 0.1 mol, from example 41) is added to a solution of potassium methylate (0.22 mol) in anhydrous methyl alcohol (65 mL) and stirred for 15 minutes at ambient temperature. Dimethyl malonate (12.6 mL, 0.11 mol) is added and the mixture is heated to reflux for 4 hours. After cooling, the resulting suspension is diluted with methyl alcohol (50 mL).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-a5b8139e7d7b4fdeafcfaf9f45d25873
Source dataset
uspto-grants-1998_12
Patent number
US05849758

Reaction notes

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