N-(4-Methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine → 4-[[4-(3-Pyridinyl)-2-pyrimidinyl]amino]phenol

HRID 2352177Notes

Reaction equation

HRID 2352177 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1>Br>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[N:15]=2)[CH:17]=1

Participants

3

Reactant 1

HCID 14346975N-(4-Methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 143471904-[[4-(3-Pyridinyl)-2-pyrimidinyl]amino]phenol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A 25.0 g portion of N-(4-methoxyphenyl)-4-(3-pyridinyl)-2-pyrimidinamine was dissolved in 200 ml of 48% hydrobromic acid and stirred overnight under an argon atmosphere. The mixture was then heated on a steam bath for 7 hours, cooled overnight and evaporated at 60° C. The residue was basified with 200 ml of saturated potassium bicarbonate solution and stirred for 1.5 hours. The solid was collected, washed with water, dried and recrystallized from hot absolute ethanol, giving 19.1 g of the desired product, mp 223°-225° C.

Workup

  1. temperatureThe mixture was then heated on a steam bath for 7 hours
  2. temperaturecooled overnight
  3. customevaporated at 60° C
  4. stirringstirred for 1.5 hours
  5. customThe solid was collected
  6. washwashed with water
  7. customdried
  8. customrecrystallized from hot absolute ethanol

Sources & evidence

ORD record
ord-83ccaa319ea244c4a4dc7de81e4c1931
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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