Dimethylformamide → 4-Chloro-6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidine

HRID 1891008Notes

Reaction equation

HRID 1891008 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:19]=[CH:18][NH:17][C:16](=O)[CH:15]=1.CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>ClCCl.O1CCOCC1>[Cl:29][C:16]1[CH:15]=[C:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[N:19]=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1361275726-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one

Product 1

HCID 585505244-Chloro-6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidineYield 100.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3H-pyrimidin-4-one (0.375 g, 1.37 mmol) in dichloromethane (5 mL) and dioxane (5 mL) was added DMF (0.05 mL) followed by a solution of oxalyl chloride (0.5 mL, 4 mmol). After stirring for 1 h, the mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate (25 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum to give 0.4 g (99%) 4-chloro-6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidine as colorless oil.

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate (25 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-31e8c13856ad4041a3a1d89713610d3d
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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