Methyl(4-aminophenoxy)acetate → 4-(3'-Chloro-4'-fluoroanilino)-6-(4'-methoxycarbonylmethoxyanilino)pyrimidine

HRID 1417979Notes

Reaction equation

HRID 1417979 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)[CH:3]=1.[CH3:17][O:18][C:19]([CH2:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)=[O:20]>>[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[F:15])[NH:8][C:4]1[CH:3]=[C:2]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([O:22][CH2:21][C:19]([O:18][CH3:17])=[O:20])=[CH:24][CH:25]=2)[N:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 6422115Methyl(4-aminophenoxy)acetateHCID 542586564-(3-Chloro-4-fluorophenylamino)-6-chloropyrimidine

Product 1

HCID 537444604-(3'-Chloro-4'-fluoroanilino)-6-(4'-methoxycarbonylmethoxyanilino)pyrimidineYield 26%

Procedure

Using an analogous reaction procedure to that described in Example 6, 6-chloro-4-(3'-chloro-4'-fluoroanilino)pyrimidine (0.258 g) was reacted with 4-methoxycarbonylmethoxyaniline (0.195 g). The reaction product was chromatographed on silica and precipitated from a mixture of methylene chloride, methanol and hexane to give 4-(3'-chloro-4'-fluoroanilino)-6-(4'-methoxycarbonylmethoxyanilino)pyrimidine in 26% yield, m.p. 191°-193° C.

Workup

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

Sources & evidence

ORD record
ord-b3cdd8c6423e44b6b359046cf640375e
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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