Sodium hydride → 5-[4-(2-[2,2,2-Trifluoroethyl]guanidino)pyrimid-2-yloxy]valeronitrile

HRID 978392Notes

Reaction equation

HRID 978392 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][OH:7])#[N:2].[H-].[Na+].[F:10][C:11]([F:27])([F:26])[CH2:12][N:13]=[C:14]([NH2:25])[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18](S(C)=O)[N:17]=1>C(O)(C)(C)C>[F:27][C:11]([F:10])([F:26])[CH2:12][N:13]=[C:14]([NH2:25])[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[N:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 108878405-HydroxypentanenitrileHCID 212797752-Methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine

Product 1

HCID 212797715-[4-(2-[2,2,2-Trifluoroethyl]guanidino)pyrimid-2-yloxy]valeronitrileYield 67.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-Cyanobutanol (10 g.) was added to sodium hydride (2.75 g.) in t-butanol (95 ml.) and the solution warmed to 40°. 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methylsulphinylpyrimidine (11.24 g.) was added over 10 minutes and the solution kept at 40° for 2 hours then at room temperature for 18 hours. The solvent was removed under vacuum and the residue washed with water, then ether to give 5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yloxy]valeronitrile (8.5 g.), m.p. 134°-136°.

Workup

  1. temperaturethe solution warmed to 40°
  2. waitat room temperature for 18 hours
  3. customThe solvent was removed under vacuum
  4. washthe residue washed with water

Sources & evidence

ORD record
ord-89bf6c9732864da3928249204daa9682
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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