Pyridine → HCID 178485210, compound

HRID 1902288Notes

Reaction equation

HRID 1902288 reaction equation
[Br:1]Br.[F:3][C:4]([F:30])([F:29])[CH2:5][N:6]=[C:7]([NH2:28])[NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:26][CH3:27])=[N:21][S:22]([CH3:25])(=[O:24])=[O:23])[N:10]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:14]1[C:9]([NH:8][C:7]([NH2:28])=[N:6][CH2:5][C:4]([F:29])([F:3])[F:30])=[N:10][C:11]([S:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:26][CH3:27])=[N:21][S:22]([CH3:25])(=[O:23])=[O:24])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 1784852114-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[3-(2-methylsulphonyl-3-methylguanidino)propylthio]pyrimidine

Product 1

HCID 178485210HCID 178485210, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.064 g.) in methylene chloride (2 ml.) was added dropwise over 15 minutes to a stirred solution of 4-[2-(2,2,2-trifluoroethyl)-guanidino]-2-[3-(2-methylsulphonyl-3-methylguanidino)-propylthio]pyrimidine (0.176 g.) and pyridine (0.2 ml.) in methylene chloride (10 ml.), and the mixture stirred at room temperature for one hour. The solution was evaporated to dryness, and the residue purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 5-bromo-4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[3-(2-methylsulphonyl-3-methylguanidino)propylthio]-pyrimidine (0.12 g.), m.p. 166°-167° after recrystallisation from ethanol.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-b3b561621c744379a4af955ed93f7ec9
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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