Lithium Hydroxide → HCID 136377078, compound

HRID 1409556Notes

Reaction equation

HRID 1409556 reaction equation
[OH-].[Li+].[OH:3][C:4]1[C:5]([C:23]([O:25]C)=[O:24])=[N:6][C:7]([CH2:11][C:12]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:8][C:9]=1[OH:10]>O.O1CCCC1>[OH:3][C:4]1[C:9](=[O:10])[NH:8][C:7]([CH2:11][C:12]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:14][CH2:15][CH2:16]2)=[N:6][C:5]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178499080HCID 178499080, compound

Product 1

HCID 136377078HCID 136377078, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide (7.66 mg, 320 μmol) in water (1.00 ml) was added to a stirred mixture of methyl 5,6-dihydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylate (0.035 g, 107 μmol) in tetrahydrofuran (THF) (4 ml). The mixture was stirred at RT for 72 h and then quenched with amberlyst (H+) IE resin, filtered and evaporated to dryness. The residue was triturated with EtOAc and dried under vacuum to give the title product as a white solid (0.012 g; 32%). LCMS: m/z=315 (MH+).

Workup

  1. customquenched with amberlyst (H+) IE resin
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue was triturated with EtOAc
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1b47c89ad45547e29f127f5fe0279c67
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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