m-Toluidine → 4-[4'-Hydroxyanilino]6-(3'-methylanilino)pyrimidine

HRID 1417989Notes

Reaction equation

HRID 1417989 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]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:17]([CH3:16])[CH:18]=3)[N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 180091284-(4-Hydroxyanilino)-6-chloropyrimidine

Product 1

HCID 544096924-[4'-Hydroxyanilino]6-(3'-methylanilino)pyrimidine

Procedure

Using an analogous reaction procedure to that described in Example 6, 6-chloro-4-(4'-hydroxyanilino)pyrimidine (3.2 g) was reacted with 3-methylaniline (5 ml). The product so obtained was triturated under methylene chloride. The solid so obtained was filtered off and extracted with hot water. On cooling a solid precipitated from the aqueous solution. The solid was extracted from the aqueous solution with ethyl acetate, washed with water and with brine, dried (MgSO4) and recrystallised from a mixture of ethyl acetate and hexane to give 4-(4'-hydroxyanilino)-6-(3'-methylanilino)pyrimidine (0.15 g), m.p. 242°-245° C.;

Workup

  1. customan analogous reaction procedure to
  2. customThe product so obtained
  3. customwas triturated under methylene chloride
  4. customThe solid so obtained
  5. filtrationwas filtered off
  6. extractionextracted with hot water
  7. temperatureOn cooling a solid
  8. customprecipitated from the aqueous solution
  9. extractionThe solid was extracted from the aqueous solution with ethyl acetate
  10. washwashed with water and with brine
  11. dry with materialdried (MgSO4)
  12. customrecrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5baf2a60bc2f4f9185278442694f86e1
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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