Lithium Hydroxide → [3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-phenyl]-methanol

HRID 426100Notes

Reaction equation

HRID 426100 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[C:18]([CH3:20])[CH:19]=2)[CH2:12][O:13]C(=O)C)[C:5]([CH:21]([CH3:23])[CH3:22])=[C:4]([Cl:24])[N:3]=1.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:12][OH:13])[CH:17]=[C:18]([CH3:20])[CH:19]=2)[C:5]([CH:21]([CH3:22])[CH3:23])=[C:4]([Cl:24])[N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59184647Acetic acid 3-(2,6-dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzyl ester

Product 1

HCID 59184707[3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-phenyl]-methanolYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4) (5 g, 13.54 mmol) in THF (20 ml) at room temperature, was added lithium hydroxide (649 mg, 27 mmol) followed by distilled water (20 ml). After stirring for 23 hr., THF was removed in vacuo and the residue was partitioned between dichloromethane and water. The organic layer was taken, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:4 to 1:1)) to afford 2.92 g (66%) of a white solid; m.p. 140-141° C.; 1H NMR (200 MHz, CDCl3) δ 1.40 (6H, d, J=7.4 Hz), 1.76 (1H, t, J=5.6 Hz), 2.39 (3H, s), 3.58 (1H, m), 4.69 (2H, d, J=5.6 Hz), 6.84 (1H, s), 6.95 (1H, s), 7.09 (1H, s).

Workup

  1. distillationby distilled water (20 ml)
  2. custom, THF was removed in vacuo
  3. customthe residue was partitioned between dichloromethane and water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:4 to 1:1))

Sources & evidence

ORD record
ord-edabaa0c302244d1ba7d36614cb68675
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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