Sodium hydride → HCID 79632468, compound

HRID 2409091Notes

Reaction equation

HRID 2409091 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([Cl:18])=[CH:13][N:12]=1>CN(C=O)C.C1COCC1>[Cl:10][C:11]1[N:16]=[C:15]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[C:14]([Cl:18])=[CH:13][N:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 79632468HCID 79632468, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydro-4-pyranol (0.36 g, 3.54 mmol) in DMF (5 mL) was added sodium hydride (60% dispersion, 0.17 g, 4.25 mmol). The resulting mixture was added to a solution of 2,4,5-trichloropyrimidine (650 mg, 3.5 mmol) in THF at 0° C. The combined mixture was then allowed to warm to room temperature. To the reaction was then added water and the product was extracted with a 1:1 EtOAc-Heptane mixture. The extract was then dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (0-30% EtOAc in heptane) to give 2,5-dichloro-4-(tetrahydro-2H-pyran-4-yloxy)pyrimidine. 1H-NMR (CDCl3): δ 8.33 (s, 1H), 5.42 (m, 1H), 4.09-3.90 (m, 2H), 3.65 (m, 2H), 2.19-1.99 (m, 2H), 1.87 (m, 2H).

Workup

  1. extractionadded water and the product was extracted with a 1:1 EtOAc-Heptane mixture
  2. dry with materialThe extract was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-be9d2c64372e4a6b8b5988330562624d
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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