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

HRID 859109Notes

Reaction equation

HRID 859109 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.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]([NH2:29])=[NH:28])[CH:23]=[CH:24][CH:25]=1.[OH-].[Li+]>CC(O)CC>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]2[N:29]=[C:5]([C:7]3[C:8]([Cl:13])=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:4]=[CH:3][N:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 533963053-Dimethylamino-1-(2-chloro-3-pyridyl)-2-propen-1-oneHCID 178491134HCID 178491134, compound

Product 1

HCID 85993058N-[3-methoxy-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamineYield 78%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-chloro-3-pyridyl)-2-propen-1-one (3.50 g, 16.5 mmol), 3-methoxy-phenyl-guanidine nitrite (3.70 g, 16.2 mmol), lithium hydroxide (412 mg, 16.5 mmol) in 2-butanol (15 mL) is heated to reflux overnight. The reaction mixture is cooled to room temperature, concentrated and water (60 mL) is added. The resultant solid is filtered, washed with water, isopropanol and dried to give N-[3-methoxy-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine (3.95 g); ESI-MS (m/z): 313 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionwater (60 mL) is added
  5. filtrationThe resultant solid is filtered
  6. washwashed with water, isopropanol
  7. customdried

Sources & evidence

ORD record
ord-04ac867d07cc418b90bdb5696e02e39b
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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