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

HRID 1902292Notes

Reaction equation

HRID 1902292 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 2 N aqueous acetic acid. The solution was washed with ether, basified with 17 N 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-2abb7c230f0a4ebfbcec1623b4906e27
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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