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

HRID 34774

反応式

HRID 34774 の反応式
[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

参加物

4

反応物 3

HCID 1049PyridineHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178485067HCID 178485067、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fde28169ae7b4666a018551f7f1d8772
出典データセット
uspto-grants-1988_08
特許番号
US04762932

関連ノート

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