Lithium Hydroxide → HCID 59128649, compound

HRID 1991003Notes

Reaction equation

HRID 1991003 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([C:11]2[C:22](=[O:23])[N:21]([CH3:24])[C:14]3[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][C:6]=1[C:11]1[C:22](=[O:23])[N:21]([CH3:24])[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59128631HCID 59128631, compound

Product 1

HCID 59128649HCID 59128649, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzoic acid methyl ester (1.0 g, 2.81 mmol) was dissolved in 4 mL THF, and 1.0 M aqueous LiOH (2.8 mL, 2.81 mmol) was added. The reaction mixture was stirred at room temperature for 100 hours, then was partitioned between diethyl ether and water. The aqueous layer was acidified by addition of 5% aqueous HCl, and the resulting precipitate was collected by filtration, washed with water, and dried under vacuum to provide 820 mg of 4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzoic acid MS (M+H)=342.

Workup

  1. customwas partitioned between diethyl ether and water
  2. additionThe aqueous layer was acidified by addition of 5% aqueous HCl
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-656a13a84ab04258aec1b9c090410345
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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