Ammonia → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(4-aminobut-2-ynylthio)pyrimidine

HRID 542482ノート

反応式

HRID 542482 の反応式
[F:1][C:2]([F:31])([F:30])[CH2:3][NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][C:15]#[C:16][CH2:17][N:18]2C(=O)C3=CC=CC=C3C2=O)[N:8]=1.C[N:33](C=O)C.N>CCO>[F:31][C:2]([F:1])([F:30])[CH2:3][N:4]=[C:5]([NH2:33])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][C:15]#[C:16][CH2:17][NH2:18])[N:8]=1

参加物

5

反応物 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 540628734-[3-(2,2,2-Trifluoroethyl)thioureido]-2-(4-phthalimidobut-2-ynylthio)pyrimidine

生成物 1

HCID 202086904-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(4-aminobut-2-ynylthio)pyrimidine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-[3-(2,2,2-trifluoroethyl)thioureido]-2-(4-phthalimidobut-2-ynylthio)pyrimidine (0.37 g.), DMF (10 ml.), saturated ethanolic ammonia (1 ml.), EtOH (10 ml.) and yellow mercuric oxide (0.32 g.) was stirred at room temperature for 2 hours and then filtered and the filtrate evaporated to dryness. The residue was treated with EtOH (20 ml.) and 98% hydrazine hydrate (1 ml.) and the mixture heated under reflux for 1 hour and then evaporated to dryness. The residue was stirred with N aqueous HCl and then filtered. The filtrate was basified with 10N aqueous NaOH and the mixture extracted four times with ether. The combined extracts were dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(4-aminobut-2-ynylthio)pyrimidine (0.17 g.) characterised as the bis hydrogen maleate, m.p. 153°-155° (decomp.)

後処理

  1. filtrationfiltered
  2. customthe filtrate evaporated to dryness
  3. additionThe residue was treated with EtOH (20 ml.) and 98% hydrazine hydrate (1 ml.)
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 1 hour
  6. customevaporated to dryness
  7. stirringThe residue was stirred with N aqueous HCl
  8. filtrationfiltered
  9. extractionthe mixture extracted four times with ether
  10. customThe combined extracts were dried
  11. customevaporated to dryness

出典と根拠

ORDレコード
ord-d357c8e564b44ca49deae8a3846dd30e
出典データセット
uspto-grants-1987_04
特許番号
US04657908

反応ノート

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