2-Chloropyrimidine → HCID 21298810, compound

HRID 364315Notes

Reaction equation

HRID 364315 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])[N:11]=1.Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1>C(#N)C>[F:19][C:2]([F:1])([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[N:11]=1

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazole

Product 1

HCID 21298810HCID 21298810, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole (0.45 g.) and 2-chloropyrimidine (0.18 g.) was heated under reflux in acetonitrile (5 ml.) for 16 hours. The reaction mixture was then evaporated to dryness and the residue purified by medium pressure liquid chromatography on silica gel using chloroform/methanol/ammonia 1900:100:5 v/v/v as eluant. The appropriate fraction was evaporated to dryness and the residue recrystallised from acetonitrile to give 2-(4-[2-(2-[2,2,2-trifluoroethyl]guanidino)thiazol-4-yl]butylamino)pyrimidine (0.29 g.), m.p. 173°-175°.

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was then evaporated to dryness
  3. customthe residue purified by medium pressure liquid chromatography on silica gel
  4. customThe appropriate fraction was evaporated to dryness
  5. customthe residue recrystallised from acetonitrile

Sources & evidence

ORD record
ord-0216500d19124b55a58db75efd6a2ce8
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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