Hydrochloric Acid → 2-(6-Cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetic acid

HRID 1868485Notes

Reaction equation

HRID 1868485 reaction equation
[C:1]([C:3]1[C:4]([CH3:25])=[N:5][C:6]2[N:7]([CH:17]=[C:18]([CH2:20][C:21]([O:23]C)=[O:22])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])#[N:2].[Li+].[OH-].Cl>C1COCC1>[C:1]([C:3]1[C:4]([CH3:25])=[N:5][C:6]2[N:7]([CH:17]=[C:18]([CH2:20][C:21]([OH:23])=[O:22])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57982479Methyl 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate

Product 1

HCID 579824512-(6-Cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetate (Example 162, Step 4, 260 mg, 0.7 mmol) in THF (1.4 mL) was added LiOH (2.0 M in H2O, 7 mL, 14 mmol). After 18 min, the clear brown reaction was adjusted to pH 2 using hydrochloric acid (2 N in H2O, 2.35 mL, 4.7 mmol). The solution became less dark and a precipitate formed. The mixture was extracted with EtOAc (3×7 mL), the combined organic extracts were back-washed with 5 mL water, and then dried with MgSO4. Filtration and concentration provided 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetic acid (239 mg, 95%) as a yellow-brown foam.

Workup

  1. customthe clear brown reaction
  2. customa precipitate formed
  3. extractionThe mixture was extracted with EtOAc (3×7 mL)
  4. washthe combined organic extracts were back-washed with 5 mL water
  5. dry with materialdried with MgSO4
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-fe7ab5837da447db93482c5cb7c12d2a
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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