1,3-Propanediamine → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylamino)pyrimidine

HRID 34790Notes

Reaction equation

HRID 34790 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.[NH2:19][CH2:20][CH2:21][CH2:22][NH2:23]>>[F:1][C:2]([F:18])([F:17])[CH2:3][N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[N:8]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 212797752-Methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine

Product 1

HCID 212987444-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylamino)pyrimidine

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-methylsulphinylpyrimidine (0.3 g.) and 1,3-diaminopropane (1 ml.) was heated to 90° for 3 hours. The mixture was evaporated to dryness and the residue taken up in 2N aqueous acetic acid. The solution was washed with ether, basified with 17N NaOH and the mixture extracted five times with ether. The combined ether extracts were dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylamino)pyrimidine (0.27 g.) which was characterised as the tris hydrogen maleate, m.p. 159° after recrystallisation from acetone.

Workup

  1. temperaturewas heated to 90° for 3 hours
  2. customThe mixture was evaporated to dryness
  3. washThe solution was washed with ether
  4. extractionthe mixture extracted five times with ether
  5. dry with materialThe combined ether extracts were dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-45e1a05f2209452c97530c1cf8d9be1b
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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