Lithium hydroxide, monohydrate → HCID 58458905, compound

HRID 390341Notes

Reaction equation

HRID 390341 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:11][C:10]=1[C:22]([O:24]CC)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>C1COCC1.O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:11][C:10]=1[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67434393HCID 67434393, compound

Product 1

HCID 58458905HCID 58458905, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of ethyl 5-(benzyloxy)-2-cyclopentyl-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate (prepared according to the procedure in Naidu, B. N. Synlett, 2008;) (1.1 g, 3.1 mmol) and LiOH.H2O (0.25 g, 6 mmol) in 2:1 THF/H2O (15 mL) was heated at 80° C. for 1 h then cooled. The reaction mixture concentrated and the residue acidified with 1 N aq. HCl and the resulting solid isolated by filtration to yield the title compound (0.98 g, 97% yield) as a white solid. 1HNMR (500 MHz, CDCl3) δ: 7.56-7.52 (2H, m), 7.36-7.28 (3H, m), 5.42 (2H, s), 3.59 (3H, s), 3.20-3.14 (1H, m), 2.08-2.01 (2H, m), 1.93-1.78 (4H, m), 1.74-1.67 (2H, m). HRMS (M+H) calcd for C18H21N2O4: 329.1501. found: 329.1489.

Workup

  1. customprepared
  2. temperaturethen cooled
  3. concentrationThe reaction mixture concentrated
  4. customthe resulting solid isolated by filtration

Sources & evidence

ORD record
ord-3b38f2e5a9b641bc9086dec87d0faf0f
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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