Sodium Acetate → Acetic acid 3-(2,6-dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzyl ester

HRID 426099Notes

Reaction equation

HRID 426099 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[O:6][C:7]1[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([Cl:16])[N:10]=[C:9]([Cl:17])[N:8]=1.[C:22]([O-:25])(=[O:24])[CH3:23].[Na+]>CN(C=O)C>[Cl:17][C:9]1[N:8]=[C:7]([O:6][C:5]2[CH:4]=[C:3]([CH:20]=[C:19]([CH3:21])[CH:18]=2)[CH2:2][O:25][C:22](=[O:24])[CH3:23])[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([Cl:16])[N:10]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 591846894-(3-Bromomethyl-5-methyl-phenoxy)-2,6-dichloro-5-isopropyl-pyrimidine

Product 1

HCID 59184647Acetic acid 3-(2,6-dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzyl esterYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (3) (14.4 g, 36.9 mmol) in anhydrous DMF (50 ml), was added sodium acetate (6.05 g, 73.8 mmol) and the mixture was stirred in an oil bath (90˜100° C.) for overnight. After cooling to room temperature, the mixture was partitioned between ether and water. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:9 to 1:4)) to afford 10 g (73%) of a white solid. m.p. 76-77° C.; 1H NMR (200 MHz, CDCl3) δ 1.41 (6H, d, J=7.2 Hz), 2.12 (3H, s), 2.39 (3H, s), 3.58 (1H, m), 5.09 (2H, s), 6.88 (1H, s), 6.93 (1H, s), 7.08 (1H, s).

Workup

  1. customthe mixture was partitioned between ether and water
  2. washwashed with water twice
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:9 to 1:4))

Sources & evidence

ORD record
ord-3f58e3fc82e24e11ad6977179d9f9b49
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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