Sodium hydride → HCID 86761731, compound

HRID 2194602Notes

Reaction equation

HRID 2194602 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.[H-].[Na+].[Br:8][C:9]1[C:10](Cl)=[N:11][C:12]([Cl:16])=[N:13][C:14]=1[CH3:15]>C1COCC1>[Br:8][C:9]1[C:14]([CH3:15])=[N:13][C:12]([Cl:16])=[N:11][C:10]=1[O:5][CH:3]1[CH2:4][O:1][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 45918375-Bromo-2,4-dichloro-6-methylpyrimidineHCID 9942117Oxetan-3-ol

Product 1

HCID 86761731HCID 86761731, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of oxetan-3-ol (0.368 g, 4.96 mmol) in anhydrous THF (16 mL) at 0° C. was added NaH (60% in mineral oil, 213 mg, 5.32 mmol). The mixture was stirred at 0° C. for 20 min, then 5-bromo-2,4-dichloro-6-methylpyrimidine (0.800 g, 3.30 mmol) was added to the mixture at 0° C. and stirred for 5 min. After this time the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue was purified using ISCO chromatography (24 g silica gel, 1-25% EtOAc in hexanes in 40 min) to give the title compound (0.566 g, 61%) as a white oil. 1H NMR (CDCl3, 500 MHz) δ 5.71-5.66 (m, 1H), 5.030-4.99 (m, 2H), 4.79-4.76 (m, 2H), 2.59 (s, 3H).

Workup

  1. stirringstirred for 5 min
  2. customAfter this time the reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. customISCO chromatography (24 g silica gel, 1-25% EtOAc in hexanes in 40 min)

Sources & evidence

ORD record
ord-ded43c6086e140c8a0ed330e43c54bc6
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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