4-(2-Methoxyethoxy)aniline → 4-(3'-Chloro-4'-fluoroanilino)-6-[4'-(2-methoxyethoxy)anilino]pyrimidine

HRID 1417980Notes

Reaction equation

HRID 1417980 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][CH2:19][CH2:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>>[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:26][C:25]2[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][O:18][CH3:17])=[CH:28][CH:27]=2)[N:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 38798854-(2-Methoxyethoxy)anilineHCID 542586564-(3-Chloro-4-fluorophenylamino)-6-chloropyrimidine

Product 1

HCID 701878224-(3'-Chloro-4'-fluoroanilino)-6-[4'-(2-methoxyethoxy)anilino]pyrimidineYield 49%

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-(2-methoxyethoxy)aniline (0.206 g). The reaction product was chromatographed on silica and precipitated from a mixture of methylene chloride and hexane to give 4-(3'-chloro-4'-fluoroanilino)-6-[4'-(2-methoxyethoxy)anilino]pyrimidine in 49% yield, m.p. 208°-210° C.;

Workup

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

Sources & evidence

ORD record
ord-a92ce9f60426473bb5ea9c221914f855
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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