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

HRID 364294

Reaction equation

HRID 364294 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-c66344abbf834f099a96d4f5dfc76961
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Linked notes

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