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

HRID 364290Notes

Reaction equation

HRID 364290 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-646353476b0143f19f831ad8ccb883e8
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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