Methanesulfonic Acid → HCID 178432672, compound

HRID 129021Notes

Reaction equation

HRID 129021 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH3:36])[C:5]2[C:11]([OH:12])=[CH:10][C:9](=[O:13])[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[N:31](C(C)(C)C)[N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:6]=2[N:7]=1.CS(O)(=O)=[O:39].[OH-:42].[K+]>C1(C)C=CC=CC=1>[OH2:12].[CH3:1][C:2]1[N:3]=[C:4]([CH3:36])[C:5]2[C:11]([OH:12])=[CH:10][C:9](=[O:13])[N:8]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:28][N:29]=[N:30][N:31]=4)=[CH:19][CH:20]=3)[C:6]=2[N:7]=1.[OH2:39].[OH2:42].[CH3:1][C:2]1[N:3]=[C:4]([CH3:36])[C:5]2[C:11]([OH:12])=[CH:10][C:9](=[O:13])[N:8]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:28][N:29]=[N:30][N:31]=4)=[CH:19][CH:20]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14797Potassium HydroxideHCID 54699159HCID 54699159, compound

Product 1

HCID 178432672HCID 178432672, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,4-dimethyl-5-hydroxy-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-8H-pyrido[2,3-d]pyrimidin-7-one (925 mg, 1.92 mmol), methanesulfonic acid (1.84 g, 19.2 mmol), and toluene (10 mL) was heated under reflux for 28 h. 1N KOH (25 mL) was added and the mixture was extracted twice with EtOAC (discarded). The aqueous phase was acidified to pH 4 with 1N HCl and the precipitate (560 mg) was collected by filtration. Recrystallizationfrom EtOH/water gave 424 mg (52%) of product as an off-white solid, mp 278-280 (dec).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 28 h
  3. extractionthe mixture was extracted twice with EtOAC (discarded)
  4. filtrationthe precipitate (560 mg) was collected by filtration

Sources & evidence

ORD record
ord-6aeb74f3508246c9b9a3204ce41cbc05
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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