Water → N-[4-[2-[bis(1-Methylethyl)amino]ethoxy]phenyl]-4-(3-pyridinyl)-2-pyrimidinamine

HRID 2352183Notes

Reaction equation

HRID 2352183 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[N:8]=2)[CH:2]=1.Cl.[CH:22]([N:25]([CH2:29][CH2:30]Cl)[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].[OH-].[Na+].O>CN(C)C=O>[CH3:23][CH:22]([N:25]([CH:26]([CH3:28])[CH3:27])[CH2:29][CH2:30][O:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:9]2[N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[CH:15][CH:16]=1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 143471904-[[4-(3-Pyridinyl)-2-pyrimidinyl]amino]phenol

Product 1

HCID 15653017N-[4-[2-[bis(1-Methylethyl)amino]ethoxy]phenyl]-4-(3-pyridinyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 2.64 g portion of 4-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenol was dissolved in 60 ml of dimethylformamide by warming on a steam bath and then cooled. A 2.0 g portion of diisopropylaminoethyl chloride hydrochloride was added and dissolved with stirring. A 20 ml portion of 5N sodium hydroxide was added dropwise over 5 minutes, then 5 ml of water was added and the mixture was stirred for 20 hours. The mixture was then heated on a steam bath for 30 minutes, allowed to stand 48 hours and then evaporated. The residual gum was purified by flash dry column chromatography on silica gel eluting fractions 1-3 with methanol and fractions 4-6 with 1% methanol in chloroform. Fractions 4-6 were combined and evaporated, giving 500 mg of the desired product.

Workup

  1. temperatureby warming on a steam bath
  2. temperaturecooled
  3. dissolutiondissolved
  4. stirringthe mixture was stirred for 20 hours
  5. temperatureThe mixture was then heated on a steam bath for 30 minutes
  6. customevaporated
  7. customThe residual gum was purified by flash
  8. dry with materialdry column chromatography on silica gel eluting fractions 1-3 with methanol and fractions 4-6 with 1% methanol in chloroform
  9. customevaporated

Sources & evidence

ORD record
ord-6e661de618904e88ae1a30cb02b77e5d
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

Loading…