Trimethyl orthoformate → 3-(4-Chloro-3-dimethoxymethylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978850Notes

Reaction equation

HRID 1978850 reaction equation
[CH:1]([O:6][CH3:7])([O:4][CH3:5])OC.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:38](=[O:39])[CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[N:35]([CH3:44])[C:34]2=[O:45])=[CH:29][C:28]=1C=O>C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:38](=[O:39])[CH:37]=[C:36]([C:40]([F:41])([F:43])[F:42])[N:35]([CH3:44])[C:34]2=[O:45])=[CH:29][C:28]=1[CH:1]([O:4][CH3:5])[O:6][CH3:7]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 212012252-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehydeHCID 71586775Bentonite

Product 1

HCID 212012303-(4-Chloro-3-dimethoxymethylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

170 ml of trimethyl orthoformate were added to a thoroughly stirred suspension of 136 g of montmorillonite K10 in 700 ml of anhydrous toluene, and stirring was carried out for 30 minutes. Thereafter, 68.0 g of 3-(4-chloro-3-formylphenyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine were added dropwise while cooling with ice, and the batch was stirred overnight at 25° C. The montmorillonite K10 was filtered off and washed thoroughly with toluene. The solvent, excess ortho-ester and methyl formate were distilled off under reduced pressure from the combined filtrates. The remaining oil was crystallized with petroleum ether.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe batch was stirred overnight at 25° C
  3. filtrationThe montmorillonite K10 was filtered off
  4. washwashed thoroughly with toluene
  5. distillationThe solvent, excess ortho-ester and methyl formate were distilled off under reduced pressure from the combined filtrates
  6. customThe remaining oil was crystallized with petroleum ether

Sources & evidence

ORD record
ord-ae4d3a71f0ab42599741a0e89ada5b57
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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