Hydrochloric Acid → 5-Chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid

HRID 218300Notes

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.[OH-].[Na+].[O-][Cl:17].[Na+].S([O-])([O-])=O.[Na+].[Na+].Cl>O>[Cl:17][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: 10 °C

Procedure

A 500 mL multi-neck flask with overhead stirrer, thermocouple and addition funnel was charged with 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (36 g, 0.20 mol), water (70 mL) and 50 wt. % aqueous NaOH (14.4 g, 0.18 mol). The mixture was stirred at 10° C., and 10.3% aqueous NaOCl (160 g, 0.22 mol) was added over 1.5 h with cooling to maintain the reaction mixture at 10° C. The mixture was cooled to 5° C., and sodium sulfite was added until KI-starch paper gave negative test results. Hydrochloric acid (37 wt. % in water, 44.3 g, 0.443 mol) was added at 5° C. over about 30 minutes to lower the pH to 0.8. The mixture was filtered, and the collected solid was washed with cold 1 N HCl (20 mL), and dried to constant weight in a vacuum-oven at 50° C. to give 40.9 g (95% yield) of the title compound as a solid melting at 189-190° C.

Workup

additionA 500 mL multi-neck flask with overhead stirrer, thermocouple and addition funnel
temperaturewith cooling
temperatureto maintain the reaction mixture at 10° C
temperatureThe mixture was cooled to 5° C.
customgave negative test
customresults
filtrationThe mixture was filtered
washthe collected solid was washed with cold 1 N HCl (20 mL)
customdried to constant weight in a vacuum-oven at 50° C.

Sources & evidence

ORD record: ord-687c42f987fe4d75b7999ceadb7b32c4
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198442B2

Reaction notes

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