3-Amino-1-propanol → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidine

HRID 34791Notes

Reaction equation

HRID 34791 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](S(C)(=O)=O)[N:8]=1.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24].[H-].[Na+]>C(O)(C)(C)C>[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:24][CH2:23][CH2:22][CH2:21][NH2:20])[N:8]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 24758Sodium hydrideHCID 212797704-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphonylpyrimidine

Product 1

HCID 212988144-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidineYield 47.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphonylpyrimidine (0.15 g.) was added to a mixture of 3-aminopropanol (0.075 g.), t-butanol (5 ml.) and a 50% w/w dispersion of sodium hydride in mineral oil (0.05 g.) which was stirred under an argon atmosphere. The mixture was stirred at room temperature for 2 hours, heated under reflux for 4 hours and then evaporated to dryness. The residue was partitioned between 2N aqueous acetic acid and ether, and the aqueous phase basified with 17N NaOH and extracted three times with ether. The combined ether extracts were dried and evaporated to dryness to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropyloxy)pyrimidine (0.07 g.) which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between 2N aqueous acetic acid and ether
  5. extractionextracted three times with ether
  6. dry with materialThe combined ether extracts were dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-31ecbbacedb24809b4177087bbf70ce6
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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