Sodium Hypochlorite → 5-Chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid
Reaction equation
[CH:1]1([C:4]2[NH:5][C:6](=[O:13])[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[N:9]=2)[CH2:3][CH2:2]1.[Cl:14][O-].[Na+].S(=O)(O)[O-].[Na+]>O>[Cl:14][C:7]1[C:6](=[O:13])[NH:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:9][C:8]=1[C:10]([OH:12])=[O:11]Participants
Conditions
- Temperature
- 9 °C
Procedure
To a mixture of 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e. the product of Step A1 or A2) (184 g, 1.02 mol) in water (45 mL) and concentrated hydrochloric, acid (292 g, 3 mol) at 8-12° C. was added dropwise aqueous sodium hypochlorite solution, (8.4%, 1.02 kg, 1.15 mol) over 2 h so that with cooling the reaction mixture was maintained at 8-10° C. The mixture was then held at 10-12° C. for 1 h and the conversion was monitored by HPLC. When less than 5% of the starting material remained solid sodium bisulfite was added until a negative KI starch paper test was obtained. The mixture was cooled to 5° C., and the suspended product was isolated by filtration and washed with a minimum amount of cold water. The product was then dried to constant weight in vacuum-oven at 50° C. to afford the title compound (194 g); m.p. 189-190° C.
Workup
- concentrationconcentrated hydrochloric
- temperaturewith cooling the reaction mixture
- customwas obtained
- temperatureThe mixture was cooled to 5° C.
- customthe suspended product was isolated by filtration
- washwashed with a minimum amount of cold water
- customThe product was then dried to constant weight in vacuum-oven at 50° C.
Sources & evidence
- ORD record
- ord-4eadabf1fb634b8b852c75df87c7aa67
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863220B2
Reaction notes
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