Lithium hydroxide, monohydrate → HCID 11681260, compound

HRID 628825Notes

Reaction equation

HRID 628825 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[C:14]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)[CH:13]=[CH:12][N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69230482HCID 69230482, compound

Product 1

HCID 11681260HCID 11681260, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

Part B. A solution of ethyl 4-[2-(4-isopropyl-phenyl)-pyrimidin-4-yl]-benzoate in THF-water-ethanol (2 mL/2 mL/1 mL) is treated with lithium hydroxide hydrate (60 mg) and stirred for 12 h. The solution is evaporated, and the residue is partitioned between 1 M aq. HCl and ethyl acetate. The organic phase is washed with water (20 mL), dried over magnesium sulfate, filtered and evaporated to afford the title compound as a white solid (65 mg, 41%), m.p. 262-264° C. 1H NMR (300 MHz, acetone-d6): δ 8.96 (1H, d, J=6 Hz), 8.48 (2H, d, J=9 Hz), 8.23 (2H, d, J=9 Hz), 8.12 (2H, d, J=9 Hz), 7.98 (1H, d, J=6 Hz), 7.44 (2H, d, J=9 Hz), 3.02 (1H, heptet, J=7 Hz), 1.33 (6H, d, J=7 Hz). MS (ES+): m/e 320 (20), 319 (100). MS (ES−): m/e 318 (20), 317 (100).

Workup

  1. customThe solution is evaporated
  2. customthe residue is partitioned between 1 M aq. HCl and ethyl acetate
  3. washThe organic phase is washed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-aa838647d13644f78a6272a43cf00cc9
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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