Tetrahydrofuran → HCID 136268166, compound

HRID 1409579Notes

Reaction equation

HRID 1409579 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)=[N:4][C:3]=1[C:23]([O:25]C)=[O:24].O.[OH-].[Li+].C1COCC1>O>[OH:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)=[N:4][C:3]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 136268157HCID 136268157, compound

Product 1

HCID 136268166HCID 136268166, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a round-bottomed flask, methyl 5-hydroxy-2-((3′-methylbiphenyl-2-yl)methyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (30 mg, 85.6 μmol) and lithium hydroxide hydrate (6.5 mg, 155 μmol) were combined with THF (2 ml) and water (1 ml) to give a colorless solution. The mixture was stirred at 50° C. for one day. Amberlyst (15, ion exchange resin) was added, the mixture was stirred for 10 min, filtered and evaporated to dryness. Trituration with EtOAc and hexanes provided the title compound as a white solid (0.011 g; 34%). LCMS: m/z=337 (MH+) 90% pure.

Workup

  1. customto give a colorless solution
  2. additionAmberlyst (15, ion exchange resin) was added
  3. stirringthe mixture was stirred for 10 min
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5dfcd9b3c46b4498b8924897078fd9a6
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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