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

HRID 542482Notes

Reaction equation

HRID 542482 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.)

Workup

  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

Sources & evidence

ORD record
ord-d357c8e564b44ca49deae8a3846dd30e
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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