Lithium Hydroxide → N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine

HRID 859106Notes

Reaction equation

HRID 859106 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([Cl:13])=[N:9][CH:10]=[CH:11][CH:12]=1)=O.N(O)=O.[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[C:25]([NH:29][C:30]([NH2:32])=[NH:31])[CH:26]=[CH:27][CH:28]=1)=[O:22])[CH3:19].[OH-].[Li+]>CC(O)CC>[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[C:25]([NH:29][C:30]2[N:32]=[C:5]([C:7]3[C:8]([Cl:13])=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:4]=[CH:3][N:31]=2)[CH:26]=[CH:27][CH:28]=1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 533963053-Dimethylamino-1-(2-chloro-3-pyridyl)-2-propen-1-oneHCID 178468909HCID 178468909, compound

Product 1

HCID 86595099N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamineYield 84%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-chloro-3-pyridyl)-2-propen-1-one (810 mg, 3.86 mmol), 3-ethoxycarbonyl-phenyl-guanidine nitrite (1.07 g, 3.96 mmol), lithium hydroxide (105 mg, 4.38 mmol) in 2-butanol (20 mL) is heated to reflux overnight. The reaction mixture is cooled to room temperature, the solvent is removed and water (40 mL) is added. The solid is collected by filtration and washed with water, isopropanol and dried to give N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine (1.15 g); ESI-MS (m/z): 355.1 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. customthe solvent is removed
  4. additionwater (40 mL) is added
  5. filtrationThe solid is collected by filtration
  6. washwashed with water, isopropanol
  7. customdried

Sources & evidence

ORD record
ord-0f93d0c597764c2a9a70965064d577d9
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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