Acetyl chloride → 5-Acetyl-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione

HRID 877022Notes

Reaction equation

HRID 877022 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([CH3:10])[C:3]1=[O:11].[C:12](Cl)(=[O:14])[CH3:13]>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[C:12]([C:6]1[C:5](=[O:9])[N:4]([CH3:10])[C:3](=[O:11])[N:2]([CH3:1])[C:7]=1[CH3:8])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 260751,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 126235485-Acetyl-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of Step 1 intermediate (10.0 g, 62.893 mmol), acetyl chloride (4.47 ml, 62.893 mmol) and anhydrous zinc chloride (8.57 g, 62.893 mmol) in dry benzene (150 ml) was refluxed for 48 h. The solvent was completely evaporated under reduced pressure, diluted with water (500 ml) and extracted with chloroform (3×150 ml). The combined organic layers were washed with water (150 ml), dried (Na2SO4) and concentrated. The residue obtained was purified by silica gel column chromatography by using 30% ethyl acetate in petroleum ether to afford 4.7 g of the product as a pale yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.38 (s, 3H), 2.55 (s, 3H), 3.37 (s, 3H), 3.48 (s, 3H).

Workup

  1. customThe solvent was completely evaporated under reduced pressure
  2. additiondiluted with water (500 ml)
  3. extractionextracted with chloroform (3×150 ml)
  4. washThe combined organic layers were washed with water (150 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-108e2a2b5c7f48f493144d1355fc81d5
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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