Hydrochloric Acid → HCID 178441874, compound

HRID 2169197Notes

Reaction equation

HRID 2169197 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:26]([O:28]C(C)(C)C)=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O.O>[CH2:1]([O:8][C:9]1[C:10]([C:26]([OH:28])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:18])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:25])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178450823HCID 178450823, compound

Product 1

HCID 178441874HCID 178441874, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

tert-Butyl 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylate (55) (260 mg, 598 μmol, Eq: 1.00) was stirred in tetrahydrofuran/water. Lithium hydroxide monohydrate (126 mg, 2.99 mmol, Eq: 5) was added. The reaction mixture was heated at 85° C. for 7 hours, cooled, and stirred at room temperature for 16 hours. 1N HCl was added until precipitate forms (about 10 ml). The mixture was diluted with water, extracted three times with ethyl acetate, washed with brine and dried over magnesium sulfate. The solvent was removed on a rotary evaporator to give 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylic acid (56) as a white solid (155 mg, 68%).

Workup

  1. temperaturecooled
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-3cc2b77cf4814f0bb49373b7f1bc6b06
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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