Diethyl Ether → 5-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-yloxy)valeramidine hydrochloride

HRID 2291326Notes

Reaction equation

HRID 2291326 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][N:4]=[C:5]([NH2:22])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[NH:21])OC)[N:8]=1.[Cl-:25].[NH4+:26].CCOCC>CO>[ClH:25].[F:1][C:2]([F:24])([F:23])[CH2:3][N:4]=[C:5]([NH2:22])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH2:26])=[NH:21])[N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 21279807Methyl 5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)valerimidate

Product 1

HCID 212797305-(4-[2-(2,2,2-Trifluoroethyl)guanidino]pyrimid-2-yloxy)valeramidine hydrochlorideYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)valerimidate (1.5 g.) in MeOH (15 ml.) was treated with ammonium chloride (0.25 g.) and the solution stirred at room temperature for 2 hours. Ether was added until the solution became cloudy. Continued stirring caused precipitation of a solid which was filtered to give 5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yloxy)valeramidine hydrochloride, (1.52 g.), m.p. 156°-158°.

Workup

  1. stirringContinued stirring
  2. customprecipitation of a solid which
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-d516a44a5aca40deb1aba7d8773b3ef1
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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