HCID 131717218, compound → HCID 178441615, compound

HRID 2372843Notes

Reaction equation

HRID 2372843 reaction equation
[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:9](=[O:48])[C:8]([CH2:49][CH3:50])=[C:7]([CH3:51])[N:6]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.O.[Cl-].[Na+].O>[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:9](=[O:48])[C:8]([CH2:49][CH3:50])=[C:7]([CH3:51])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 131717218HCID 131717218, compound

Product 1

HCID 178441615HCID 178441615, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-n-butyl-3-[(2'-(N-triphenylmethyl-tetrazol-5-yl)-biphen-4-yl)-methyl]-5-ethyl-6-methylpyrimidin-4(3H)-one (from Example 5) in 4 mL acetic acid and 2 mL water was stirred at room temperature for 6 hours. The reaction mixture was diluted with brine and extracted three times with ether. The combined organic material was washed with brine, was dried over MgSO4, was stripped of solvent in vacuo, and then was MPLC'd in 1 acetic acid/39 hexane/60 ethyl acetate to give the title compound as a white foam. 1H NMR (300 MHz, CDCl3) δ7.87 (m, 1H), 7.58 (m, 1H), 7.49 (m, 1H), 7.40 (m, 1H), 7.02 (4 line m, 4H), 5.19 (br s, 2H), 2.57 (3 line m, 2H), 2.42 (4 line m, 2H), 2.24 (s, 3H), 1.63 (m, 2H), 1.34 (m, 2H), 0.96 (3 line m, 3H), 0.88 (3 line m, 3H); IR (CHCl3) 3420 (br), 3020, 1645, 1530, 1120 cm-1 ; FABMS: 429 (M+1).

Workup

  1. extractionextracted three times with ether
  2. washThe combined organic material was washed with brine
  3. dry with materialwas dried over MgSO4

Sources & evidence

ORD record
ord-1cf66c2a8576479eb16e7f1daf0a88b9
Source dataset
uspto-grants-1992_03
Patent number
US05100897

Reaction notes

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