m-Toluidine → HCID 9862590, compound

HRID 1417982Notes

Reaction equation

HRID 1417982 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]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>CN1C(=O)CCC1>[OH:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[C:20]([CH3:19])[CH:21]=3)[N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 86753852HCID 86753852, compound

Product 1

HCID 9862590HCID 9862590, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-chloro-4-[4'-(2-hydroxyethoxy)anilino]pyrimidine (1.0 g), 3-methylaniline (5 ml) and NMP (20 ml) was stirred and heated to 140° C. for 72 hours. The mixture was cooled and partitioned between ethyl acetate and water. The precipitate was removed by filtration, the ethyl acetate fraction chromatographed on silica and the combined products extracted with boiling ethyl acetate. The product was recrystallised from a mixture of ethyl acetate and hexane to give 4-[4'-(2-hydroxyethoxy)anilino]6-(3'-methylanilino)pyrimidine in 20% yield, m.p. 196°-199° C.;

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. customThe precipitate was removed by filtration
  4. customthe ethyl acetate fraction chromatographed on silica
  5. extractionthe combined products extracted with boiling ethyl acetate
  6. customThe product was recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d54734b9c59e4bfa85472fa910b2f543
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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