Sodium hydride → HCID 20246953, compound

HRID 1462338Notes

Reaction equation

HRID 1462338 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.[H-].[Na+].[OH:21][CH2:22][CH2:23][N:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>C(O)(C)(C)C>[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]([O:21][CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)[N:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 212797752-Methylsulphinyl-4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimidine

Product 1

HCID 20246953HCID 20246953, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-methanesulphinylpyrimidine (140 mg.) was added to a stirred mixture at 50° of t-butanol (10 ml.), NaH (48 mg. of a 50% w/w dispersion in oil) and 1-(2-hydroxyethyl)imidazole, and the mixture stirred at 50° for 2 hours and then evaporated to dryness. The residue was partitioned between aqueous 1N HCl and ether and the aqueous phase basified with aqueous 10N NaOH and extracted with EtOAc. The EtOAc extract was dried and evaporated to dryness and the residue recrystallised from EtOAc to give 1-[2-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)ethyl]imidazole (135 mg.), m.p. 149°-150°.

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between aqueous 1N HCl and ether
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. customwas dried
  6. customevaporated to dryness
  7. customthe residue recrystallised from EtOAc

Sources & evidence

ORD record
ord-b689b08915204bc3974ed55890edd49f
Source dataset
uspto-grants-1984_07
Patent number
US04460584

Reaction notes

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