Methoxyisopropylamine → (3-Chloro-phenyl)-{4-[2-(2-methoxy-1-methyl-ethylamino)-pyridin-4-yl]-pyrimidin-2-yl}-amine

HRID 2214483Notes

Reaction equation

HRID 2214483 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:22][CH:23]([CH3:27])[CH2:24][O:25][CH3:26]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:22][CH:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 123458MethoxyisopropylamineHCID 9905031N-(3-chlorophenyl)-4-(2-chloropyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 69666599(3-Chloro-phenyl)-{4-[2-(2-methoxy-1-methyl-ethylamino)-pyridin-4-yl]-pyrimidin-2-yl}-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (10.0 g, 0.03 mol) and 2-amino-1-methoxypropane (14.0 g, 0.16 mol) in dioxane (75 ml) is heated in an autoclave at 195° C. for 12 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography to give the title compound, m.p. 143–144° C.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced presssure
  6. customThe residue is purified by silicagel chromatography

Sources & evidence

ORD record
ord-dd89ffde4ccb470dbda8370ab6e7583a
Source dataset
uspto-grants-2006_09
Patent number
US07109197B2

Reaction notes

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