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

HRID 2413193Notes

Reaction equation

HRID 2413193 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 10 N 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-f3c6e444d322450bb4f76dc78a8d95f7
Source dataset
uspto-grants-1985_01
Patent number
US04496571

Reaction notes

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