Chlorine → 5-chloro-2-cyclopropyl-6-(diethoxymethyl)-1H-pyrimidin-4-one
Reaction equation
[Cl:1]Cl.[CH:3]1([C:6]2[NH:7][C:8]([CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:9][C:10](=[O:12])[N:11]=2)[CH2:5][CH2:4]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:9]1[C:10](=[O:12])[N:11]=[C:6]([CH:3]2[CH2:4][CH2:5]2)[NH:7][C:8]=1[CH:13]([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 29 °C
Procedure
Chlorine was carefully passed through 2-cyclopropyl-6-(diethoxymethyl)-4(1H)-pyrimidinone (i.e. the product of Example 3) (46.0 g, 0.193 mol) and sodium acetate (18.8 g, 0.229 mol) in acetic acid (185 mL). The temperature was maintained in the range of about 28-30° C. When the starting material had been consumed, the flow of chlorine was stopped immediately. Toluene (185 mL) was added, and the mixture was evaporated under reduced pressure. The process was repeated. The mixture was partitioned between ethyl acetate (450 mL) and water (50 mL). The organic layer was further washed with water (4×50 mL), dried and evaporated to leave the product as an off-white solid (51.75 g, 98% yield). Product recrystallized from hexanes had a melting point of 109-111° C.
Workup
- customWhen the starting material had been consumed
- additionToluene (185 mL) was added
- customthe mixture was evaporated under reduced pressure
- customThe mixture was partitioned between ethyl acetate (450 mL) and water (50 mL)
- washThe organic layer was further washed with water (4×50 mL)
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-5a572ebe93fa40be9367688fd1647dfb
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013155B2
Reaction notes
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