Lithium Hydroxide → HCID 68283588, compound

HRID 623997Notes

Reaction equation

HRID 623997 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([O:14]C)=[O:13])=[N:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O.CCOC(C)=O.Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=[O:13])=[N:3][CH:2]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68283130HCID 68283130, compound

Product 1

HCID 68283588HCID 68283588, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 5-(pyrimidin-4-yl)oxazole-4-carboxylate (179 mg, 0.80 mmol) in THF/H2O (1:1, 6 mL) was treated with LiOH (60 mg, 1.43 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min, then diluted with EtOAc and 1N aq. HCl-solution was added (to reach pH=1). The layers were separated and the aq. layer extracted with EtOAc (2×), EtOAc/MeOH 4:1 then DCM/MeOH 4:1. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to obtain the title compound as a solid which was used without further purification. LC-MS conditions A: tR=0.56 min, [M+H]+=192.47.

Workup

  1. additionwas added (to reach pH=1)
  2. customThe layers were separated
  3. extractionthe aq. layer extracted with EtOAc (2×), EtOAc/MeOH 4:1
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df38131140894381a0b7335882e61fe2
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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