Lithium hydroxide, monohydrate → HCID 67457997, compound

HRID 1852973Notes

Reaction equation

HRID 1852973 reaction equation
O.[OH-].[Li+].[CH3:4][N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:27][C:28]([O:30]C)=[O:29])[CH2:22][C:23]([O:25]C)=[O:24])[CH:20]=3)[N:13]3[CH:32]=[CH:33][N:34]=[C:12]3[CH:11]=2)[CH:7]=[N:6]1>O.CO>[CH3:4][N:5]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH2:27][C:28]([OH:30])=[O:29])[CH2:22][C:23]([OH:25])=[O:24])[CH:20]=3)[N:13]3[CH:32]=[CH:33][N:34]=[C:12]3[CH:11]=2)[CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86685304dimethyl 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedioate

Product 1

HCID 67457997HCID 67457997, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide hydrate (0.0813 g, 1.94 mmol) was dissolved in water (2 mL) and was added to a solution of dimethyl 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedioate (0.205 g, 0.484 mmol) in MeOH (4 mL). After stirring 3 days the reaction was concentrated to remove the MeOH and was then acidified to pH 4 with 1 N HCl (approximately 2 mL). Cooling resulted in a solid which was filtered and washed with MeOH. The filtrate was slightly concentrated to provide a second crop of product which was combined to provide 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedioic acid (125 mg, 65% yield). MS (apci) m/z=396.2 (M+H).

Workup

  1. concentrationwas concentrated
  2. customto remove the MeOH
  3. temperatureCooling
  4. customresulted in a solid which
  5. filtrationwas filtered
  6. washwashed with MeOH
  7. concentrationThe filtrate was slightly concentrated
  8. customto provide a second crop of product which

Sources & evidence

ORD record
ord-a3917e92992842cf81331db17c706903
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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