Carbon Tetrachloride → 1-[(2-Chloroethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
Reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:35]>N1C=CC=CC=1.C(OCC)(=O)C.CO>[Cl:35][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
150 mg (0.75 mmol) 1-[(2-hydroxyethoxy)methyl]-5-methyl-2,4(1H,3H)-pyrimidinedione were dissolved in 10 ml pyridine and 1 g PS-triphenylphosphine resin (3 mmol/g) and 147 μl carbontetrachloride were added. The reaction was stirred at room temperature for 3 days. The reaction mixture was diluted with a mixture of ethyl acetate and methanol and centrifuged. The supernatant was decanted and the solvent was evaporated under reduced pressure. The residue, dissolved in ethyl acetate and a small amount of methanol, was purified by flash chromatography on silica gel (ethyl acetate). The fractions containing the product were pooled and the volume was reduced to about 3 ml. Upon addition of hexane the product crystallized to give 97 mg of white crystals. MS (ISP): 217.1 (M−H+). 1H-NMR (DMSO-d6): 1.77 (d, 3H), 3.69–3.77 (m, 4H), 5.10 (s, 2H), 7.59 (d, 1H), 11,32 (s, br, 1H).
Workup
- customThe supernatant was decanted
- customthe solvent was evaporated under reduced pressure
- dissolutionThe residue, dissolved in ethyl acetate
- customa small amount of methanol, was purified by flash chromatography on silica gel (ethyl acetate)
- additionThe fractions containing the product
- additionUpon addition of hexane the product
- customcrystallized
Sources & evidence
- ORD record
- ord-54e5d0f116ba4f12ab236d7f22ec648f
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995143B2
Reaction notes
Loading…