Water → HCID 66737436, compound

HRID 1640458Notes

Reaction equation

HRID 1640458 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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178517770HCID 178517770, compound

Product 1

HCID 66737436HCID 66737436, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

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 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.

Workup

  1. extractionthe aqueous mixture was extracted twice with diethyl ether and twice with methylene chloride
  2. extractionthe aqueous phase was extracted with methylene chloride
  3. customThe organic phase was then dried
  4. customthe desiccant was removed by filtration
  5. customthe solvent was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a09ecef13b8445f69090364be1d0c938
Source dataset
uspto-grants-2012_02
Patent number
US08114875B2

Reaction notes

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