3-Furanol, tetrahydro- → HCID 79081625, compound

HRID 1028132Notes

Reaction equation

HRID 1028132 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[O:10]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([O:15][CH:12]2[CH2:13][CH2:14][O:10][CH2:11]2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 10796Cesium carbonateHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 79081625HCID 79081625, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with a solution of 2,4-dichloro-5-fluoropyrimidine (1.0 g, 5.99 mmol) in N,N′-dimethylformamide (20 ml). Tetrahydrofuran-3-ol (0.63 m, 7.19 mmol) and cesium carbonate (3.32 g, 10.18 mmol) were added and the resulting mixture was heated to 80° C. overnight. Upon completion, the mixture was diluted with ethyl acetate (20 mL) and washed with 1:1 water:brine (3×40 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by CombiFlash (ethyl acetate/hexanes) provided 374 mg (1.7 mmol, 29%) of 2-chloro-5-fluoro-4-(tetrahydrofuran-3-yloxy)pyrimidine. MS APCI: [M+H]+ m/z 219.0.

Workup

  1. washwashed with 1:1 water
  2. dry with materialThe organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by CombiFlash (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6c394c9c7d884d1c8d4d1083c119c4de
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

Loading…