Dimethylformamide → 6-Chloro-5-formyl-1,3-dimethyluracil

HRID 877011Notes

Reaction equation

HRID 877011 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[CH3:11][N:12]1[C:19](=[O:20])[CH2:18][C:16](=O)[N:15]([CH3:21])[C:13]1=[O:14]>C(OCC)(=O)C.CCCCCC>[Cl:3][C:16]1[N:15]([CH3:21])[C:13](=[O:14])[N:12]([CH3:11])[C:19](=[O:20])[C:18]=1[CH:8]=[O:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 69860Dimethylbarbituric acid

Product 1

HCID 3199716-Chloro-5-formyl-1,3-dimethyluracil

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phosphorous oxychloride (690 ml) was added slowly to dry N,N-dimethyl formamide (180 ml) at 0° C. The mixture was then allowed to warm to room temperature. 1,3-Dimethylbarbituric acid (60 g, 384.27 mmol) was added portion wise and refluxed for 45 min. The excess of phosphorous oxychloride and DMF were distilled off under reduced pressure and the viscous residue was poured into ice-cold water (2000 ml). The reaction mixture was allowed to room temperature and extracted with chloroform (3×500 ml). The combined organic extracts were dried over Na2SO4 and concentrated. The crude material obtained was then stirred in 10% ethyl acetate in hexane (150 ml) to obtain 58 g of the product as the pale yellow solid; 1H NMR (300 MHz, CDCl3) δ 3.41 (s, 3H), 3.69 (s, 3H), 10.18 (br s, 1H).

Workup

  1. temperaturerefluxed for 45 min
  2. distillationThe excess of phosphorous oxychloride and DMF were distilled off under reduced pressure
  3. additionthe viscous residue was poured into ice-cold water (2000 ml)
  4. customwas allowed to room temperature
  5. extractionextracted with chloroform (3×500 ml)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude material obtained

Sources & evidence

ORD record
ord-29627c05c8dd403482bf412306072f74
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

Loading…