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

HRID 34766

Reaction equation

HRID 34766 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-7aef71326bb040ceba7cdc7b35724503
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

Loading…