Sodium hydride → HCID 20451301, compound

HRID 1463062Notes

Reaction equation

HRID 1463062 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][OH:17])[N:8]=1.[H-].[Na+].[Cl:23][C:24]1[CH:29]=[N:28][CH:27]=[C:26]([Cl:30])[N:25]=1>C(O)(C)(C)C>[ClH:23].[Cl:30][C:26]1[N:25]=[C:24]([O:17][CH2:16][CH2:15][CH2:14][O:13][C:9]2[N:8]=[C:7]([NH:6][C:5]([NH2:18])=[N:4][CH2:3][C:2]([F:20])([F:1])[F:19])[CH:12]=[CH:11][N:10]=2)[CH:29]=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 785042,6-DichloropyrazineHCID 20451297HCID 20451297, compound

Product 1

HCID 20451301HCID 20451301, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-hydroxypropoxy)pyrimidine (293 mg.), a 50% w/w dispersion of sodium hydride in oil (72 mg.) and t-butanol (5 ml.) was stirred at 50° for 0.5 hours and then treated with 2,6-dichloropyrazine (165 mg.) and the resulting mixture was stirred at 50° for 18 hours. The mixture was evaporated to dryness and the residue stirred with a mixture of N aqueous hydrochloric acid and ether. The insoluble white solid was collected to give 6-chloro-2-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]-pyrimid-2-yloxy)propoxy]pyrazine hydrochloride (70 mg.), m.p. 167°-169°.

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringthe residue stirred with a mixture of N aqueous hydrochloric acid and ether
  3. customThe insoluble white solid was collected

Sources & evidence

ORD record
ord-33820022305f471ba582209c97f857c8
Source dataset
uspto-grants-1984_07
Patent number
US04463005

Reaction notes

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