Methanol → 1-(2-[4-(2-[2,2,2-Trifluoroethyl]guanidino)pyrimid-2-yl-methylthio]ethylamino)-2-methylaminocyclobutene-3,4-dione

HRID 1902297Notes

Reaction equation

HRID 1902297 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][NH2:17])[N:8]=1.CO.C[O:24][C:25]1[C:28](=O)[C:27](=O)[C:26]=1[O:31]C.[CH3:33][NH2:34]>C(O)C>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][NH:17][C:28]2[C:25](=[O:24])[C:26](=[O:31])[C:27]=2[NH:34][CH3:33])[N:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 212987204-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(2-aminoethyl)thiomethylpyrimidine

Product 1

HCID 212988481-(2-[4-(2-[2,2,2-Trifluoroethyl]guanidino)pyrimid-2-yl-methylthio]ethylamino)-2-methylaminocyclobutene-3,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)-guanidino]-2-(2-aminoethyl)thiomethylpyrimidine (0.31 g.), methanol (5 ml.) and 1,2-dimethoxycyclobutene-3,4-dione (0.14 g.) was stirred at room temperature for 18 hours. A 33% w/v solution of methylamine in ethanol (5 ml.) was added and the mixture left at room temperature for 18 hours and then 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 1-(2-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl-methylthio]ethylamino)-2-methylaminocyclobutene-3,4-dione (0.16 g.) characterised as the hydrogen maleate, m.p. 178°-184° after recrystallisation from a mixture of methanol and acetonitrile.

Workup

  1. additionwas added
  2. waitthe mixture left at room temperature for 18 hours
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-051a4ff556b544299b96e14bb8f885ab
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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