2-Fluoroaniline → HCID 70187536, compound

HRID 1417981Notes

Reaction equation

HRID 1417981 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.ClC1C=C(Cl)N=CN=1.OCCOC1C=CC(N)=CC=1.[F:38][C:39]1[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=1[NH2:41]>>[F:38][C:39]1[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=1[NH:41][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 95842-FluoroanilineHCID 709434,6-DichloropyrimidineHCID 808922-(4-Aminophenoxy)ethanolHCID 86753852HCID 86753852, compound

Product 1

HCID 70187536HCID 70187536, compoundYield 24%

Procedure

Using an analogous reaction procedure to that described in Example 6, 4-chloro-6-[4'-(2-hydroxyethoxy)anilino]pyrimidine (0.52 g) (prepared from the reaction of 4,6-dichloropyrimidine and 4-(2-hydroxyethoxy)aniline) was reacted with 2-fluoroaniline (1 ml). The reaction product was chromatographed on silica and recrystallised from a mixture of methylene chloride, methanol and hexane to give 4-(2'-fluoroanilino)- 6-[4'-(2-hydroxyethoxy)anilino]pyrimidine in 24% yield, m.p. 163°-166° C.;

Workup

  1. customan analogous reaction procedure to
  2. customThe reaction product was chromatographed on silica
  3. customrecrystallised from a mixture of methylene chloride, methanol and hexane

Sources & evidence

ORD record
ord-855d931db7ab41428e843b01d639e222
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

Loading…