Water → HCID 66737436, compound

HRID 1678082Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].[OH:7][C:8]1[N:13]=[C:12]([OH:14])[C:11]([F:15])=[CH:10][N:9]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.CN(C)C=O>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][N:9]1[CH:10]=[C:11]([F:15])[C:12](=[O:14])[NH:13][C:8]1=[O:7]

Participants

Conditions

Temperature: 20 °C

Procedure

2.6 g (15.0 mmol) of 1-bromo-4-chlorobutane were added dropwise to a solution of 1.95 g (15.0 mmol) of 2,4-dihydroxy-5-fluoropyrimidine in 50 ml of dimethyl sulfoxide and 20.0 ml of N,N-dimethylformamide (DMF) at 0° C. 2.07 g (15.0 mmol) of K2CO3 were added in portions over the course of 1 hour, and the mixture was stirred at 20° C. for 1 hour (dialkylated product is already identifiable). Water was then added to the reaction mixture, and the aqueous mixture was extracted twice with diethyl ether and twice with methylene chloride. The aqueous phase was adjusted to pH 3-4 with hydrochloric acid and then the aqueous phase was extracted with methylene chloride. The organic phase was then dried, the desiccant was removed by filtration, and the solvent was evaporated to dryness in vacuo; yield: 0.6 g. 1-(4-Chlorobutyl)-5-fluoropyrimidine-2,4(1H,3H)-dione was employed without further purification in the next step.

Workup

extractionthe aqueous mixture was extracted twice with diethyl ether and twice with methylene chloride
extractionthe aqueous phase was extracted with methylene chloride
customThe organic phase was then dried
customthe desiccant was removed by filtration
customthe solvent was evaporated to dryness in vacuo
custom1-(4-Chlorobutyl)-5-fluoropyrimidine-2,4(1H,3H)-dione was employed without further purification in the next step

Sources & evidence

ORD record: ord-59e10ce41e1d4458bb0697ae36126c78
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008488B2

Reaction notes

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