Ethylene Glycol → 4,6-Dichloro-5-(1,3-dioxolan-2-yl)pyrimidine

HRID 1426068Notes

Reaction equation

HRID 1426068 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH:8]2[O:13][CH2:12][CH2:11][O:9]2)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 595944404,6-Dichloro-5-(1,3-dioxolan-2-yl)pyrimidineYield 82.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Compound 4,6-Dichloro-pyrimidine-5-carbaldehyde (8.6 g, 0.049 mmol), anhydrous ethylene glycol (8.2 ml) and p-Toluene-sulfonic acid (150 mg) were mixture in benzene (200 mL) and heated under reflux for 3 hours. Concentrate under high vacuum, worked up with chloroform, water, sodium bicarbonate and sodium chloride, concentrate. The reaction mixture was purified on silica (CH2Cl2) to give 4,6-Dichloro-5-[1,3]dioxolan-2-yl-pyrimidine (8.86 g, 82.5%). 1H NMR 400 MHz CDCl3 δ (ppm): 8.8 (s, 1H), 6.3 (s, 1H), 4.3 (m, 2H,), 4.1(m, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. concentrationConcentrate under high vacuum
  4. concentrationconcentrate
  5. customThe reaction mixture was purified on silica (CH2Cl2)

Sources & evidence

ORD record
ord-5effa3fcf8414ddda864ee7c60683db1
Source dataset
uspto-grants-2015_01
Patent number
US08933083B2

Reaction notes

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