Lithium Hydroxide → HCID 66613960, compound

HRID 510045Notes

Reaction equation

HRID 510045 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([C:21]([O:23]C)=[O:22])=[CH:16][N:15]=2)=[N:6]1.[OH-].[Li+]>O1CCCC1>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([CH3:20])[C:17]([C:21]([OH:23])=[O:22])=[CH:16][N:15]=2)=[N:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66613918Methyl 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methylpyrimidine-5-carboxylate

Product 1

HCID 66613960HCID 66613960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

830 mg (2.20 mmol) of the compound from example 44A were initially charged in tetrahydrofuran (10 ml), 4.40 ml (4.40 mmol) of aqueous lithium hydroxide solution (1.0 M) were added and the suspension was stirred at RT for 90 min Subsequently, the now clear solution was concentrated and the residue was partitioned between ethyl acetate and water. The aqueous phase was adjusted to pH<7 with 1M hydrochloric acid, and a solid precipitated out. This was filtered off, washed with water and tert-butyl methyl ether, and dried under high vacuum. This gave 710 mg (89% of theory) of the title compound in solid form.

Workup

  1. concentrationthe now clear solution was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customa solid precipitated out
  4. filtrationThis was filtered off
  5. washwashed with water and tert-butyl methyl ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-418603226d5742019ee343065a7828a4
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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