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

HRID 859108Notes

Reaction equation

HRID 859108 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=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[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=3)[CH:4]=[CH:3][N:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-oneHCID 178491134HCID 178491134, compound

Product 1

HCID 54226161N-[3-methoxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamineYield 85.6%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one (2.22 g, 10.5 mmol), 3-methoxy-phenyl-guanidine nitrite (2.40 g, 10.5 mmol), lithium hydroxide (350 mg, 14.5 mmol) in 2-butanol (25 mL) is heated to reflux for 8 hours. The reaction mixture is cooled to room temperature, concentrated and water (60 mL) is added. The resultant solid is collected by filtration and washed with water, isopropanol and dried to give N-[3-methoxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (2.81 g); ESI-MS (m/z): 313 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 8 hours
  3. concentrationconcentrated
  4. additionwater (60 mL) is added
  5. filtrationThe resultant solid is collected by filtration
  6. washwashed with water, isopropanol
  7. customdried

Sources & evidence

ORD record
ord-7ce61cc3e1934c768051efe058908303
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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