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

HRID 1902293Notes

Reaction equation

HRID 1902293 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 2 N aqueous acetic acid and ether, and the aqueous phase basified with 17 N 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 2 N 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-8a2ec9f708dc4ec2aca25629da017bf5
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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