1,1,1-Trifluoro-2-isothiocyanatoethane → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[4-(3-(2,2,2-trifluoroethyl)thioureido)butyl]pyrimidine

HRID 1902267Notes

Reaction equation

HRID 1902267 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][N:4]=[C:5]=[S:6].[F:9][C:10]([F:28])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])[N:16]=1>C(#N)C>[F:28][C:10]([F:9])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:5]([NH:4][CH2:3][C:2]([F:8])([F:7])[F:1])=[S:6])[N:16]=1

Participants

4

Reactant 2

HCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 212987744-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(4-aminobutyl)pyrimidine

Product 1

HCID 212988754-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[4-(3-(2,2,2-trifluoroethyl)thioureido)butyl]pyrimidineYield 25.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trifluoroethylisothiocyanate (0.31 g.) was added to a solution of 4-[2-(2,2,2-trifluoroethyl)-guanidino]-2-(4-aminobutyl)pyrimidine (0.58 g.) in acetonitrile (5 ml.), and the solution kept at room temperature for 18 hours and then evaporated to dryness. The residual gum 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-[4-(3-(2,2,2-trifluoroethyl)thioureido)butyl]pyrimidine (0.22 g.) characterised as the hydrogen maleate, m.p. 142°-145° (after recrystallisation from acetonitrile).

Workup

  1. customevaporated to dryness
  2. customThe residual gum was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-9deb05b8fcfb4fae9babc93e5500afd4
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

Loading…