Pyridine → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine

HRID 364273Notes

Reaction equation

HRID 364273 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:13]([NH:17][CH3:18])=[N:14][C:15]#[N:16])[N:3]=1.[F:19][C:20]([F:26])([F:25])[CH2:21][N:22]=[C:23]=S.[N:27]1C=CC=CC=1>>[F:19][C:20]([F:26])([F:25])[CH2:21][N:22]=[C:23]([NH2:27])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:13]([NH:14][C:15]#[N:16])=[N:17][CH3:18])[N:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178485067HCID 178485067, compound

Product 1

HCID 212988204-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine

Procedure

A mixture of 4-amino-2-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]pyrimidine (0.5 g.), 2,2,2-trifluoroethylisothiocyanate (0.55 g.) and pyridine (10 ml.) was heated at 70° for 18 hours and then evaporated to dryness. The residue was dissolved in ethyl acetate and the solution washed with 2N aqueous acetic acid, dried and evaporated to dryness. The residue was dissolved in ethanolic ammonia (15 ml.), treated with yellow mercuric oxide (0.4 g.) and the mixture stirred at room temperature for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine (0.2 g.) characterised as the hydrogen maleate, m.p. 111°-114° (decomp.) after recrystallisation from acetonitrile.

Workup

  1. temperaturewas heated at 70° for 18 hours
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution washed with 2N aqueous acetic acid
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in ethanolic ammonia (15 ml.)
  8. additiontreated with yellow mercuric oxide (0.4 g.)
  9. filtrationThe mixture was filtered
  10. customthe filtrate evaporated to dryness
  11. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-17241b7fe8cf46ab856f67f2a7d3a08e
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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