Lithium Hydroxide → HCID 86675932, compound

HRID 572679Notes

Reaction equation

HRID 572679 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4]([C:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][N:13]=2)[N:3]=1.[OH-].[Li+]>CO.O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][N:13]=2)[N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86675933HCID 86675933, compound

Product 1

HCID 86675932HCID 86675932, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 2-methyl-6-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxylate (0.15 g, 0.505 mmol, Preparation #19) in methanol (1.5 mL) and water (0.5 mL) mixture was added lithium hydroxide (0.036 g, 1.514 mmol, Sd Fine Chem). The reaction mixture was stirred for about 10 min at RT and the organic solvent was removed under reduced pressure. The aqueous layer was acidified with 10% citric acid solution. The solid was collected by filtration, washed with water and dried under vacuum to afford 2-methyl-6-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxylic acid 0.1 g, (70.0%) as a yellow solid. 1H NMR (400 MHz, DMSO) δ 14.0 (bs, 1H), 8.16 (s, 1H), 7.42 (m, 5H), 5.92 (m, 1H), 3:98 (m, 1H), 3.45 (m, 1H), 2.72 (s, 3H), MS m/z: 284.2 (m+H)+.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d9356592e7d34277b355c06a386669c7
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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