Methanesulfonic Acid → 2-Hydroxymethyl-4-methyl-8-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129012Notes

Reaction equation

HRID 129012 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH3:36])[C:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([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:7]=2[N:8]=1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH3:36])[C:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([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[NH:31][N:30]=[N:29][N:28]=4)=[CH:17][CH:16]=3)[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 193729942-Hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 1784330362-Hydroxymethyl-4-methyl-8-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneYield 102.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (1.2 g, 2.50 mmol), methanesulfonic acid (2.40 g, 25.0 mmol), and toluene (14 mL) was heated under reflux for 20 h. The mixture was concentrated, taken up in water, and the pH was adjusted to 7-8 with 1 N NaOH. The aqueous mixture was extracted with EtOAc (discarded), acidified to pH 4 with 1N HCl, and extracted with CHCl3. The CHCl3 layers were dried (MgSO4) and concentrated to give 1.10 g of a foam. Trituration with EtOAc/acetone and recrystallization from EtOH gave 0.45 g (46%) of product as a white solid, mp 218°-220° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. concentrationThe mixture was concentrated
  4. extractionThe aqueous mixture was extracted with EtOAc (discarded)
  5. extractionextracted with CHCl3
  6. dry with materialThe CHCl3 layers were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed341cdad0434248b3e7cdf6232a16cd
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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