Potassium Carbonate → 3-butyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373242Notes

Reaction equation

HRID 373242 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([Cl:12])[NH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:32]([C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:31]=[N:30][N:29]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([Cl:12])[N:7]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:6]1=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 141001713-butyl-6-chloropyrimidine-2,4(1H,3H)-dione

Product 1

HCID 198115293-butyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-butyl-6-chloropyrimidine-2,4(1H,3H)-dione (1 g), 4-bromomethyl-2'-(N-trityltetrazol-5-yl)biphenyl (3.02 g) and potassium carbonate (0.82 g) in DMF (50 ml) was stirred at 60° C. for 4 hours. The reaction mixture was concentrated to dryness in vacuo and then the residue was dissolved in methylene chloride. The insoluble material was removed from the reaction mixture by filtration and the filtrate was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel and recrystallized from ethyl acetate-hexane to give colorless prisms (1.97 g, 59%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. customThe insoluble material was removed from the reaction mixture by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe resulting residue was purified by column chromatography on silica gel
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5826978245cf498185dbf859ac479fa2
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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