p-Toluenesulfonic acid → 3-[4-Chloro-3-(1,3-dioxan-2-yl)-phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

HRID 1978849Notes

Reaction equation

HRID 1978849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[CH:4][C:3]=1[CH:21]=[O:22].[CH2:23](O)[CH2:24][CH2:25][OH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[CH:4][C:3]=1[CH:21]1[O:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 212012252-Chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]benzaldehyde

Product 1

HCID 212012313-[4-Chloro-3-(1,3-dioxan-2-yl)-phenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g of 3-[4-chloro-3-formylphenyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine, 0.8 g of 1,3-propanediol and 0.2 g of p-toluenesulfonic acid in 100 ml of anhydrous dichloromethane was boiled for 5 hours under a water separator. The solution was washed with 10% strength sodium bicarbonate solution and water, dried over sodium sulfate and evaporated down. The residue was chromatographed over silica gel (7:3 cyclohexane/ethyl acetate).

Workup

  1. washThe solution was washed with 10% strength sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down
  4. customThe residue was chromatographed over silica gel (7:3 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-af598d3e94b9480fa2d2db114845fdb7
Source dataset
uspto-grants-2001_05
Patent number
US06239074B1

Reaction notes

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