Water → N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamine

HRID 859103Notes

Reaction equation

HRID 859103 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.[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-].[Na+].O>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[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=3)[CH:4]=[CH:3][N:31]=2)[CH:26]=[CH:27][CH:28]=1)=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 544350393-Dimethylamino-1-(2-chloro4-pyridyl)-2-propen-1-oneHCID 178468909HCID 178468909, compound

Product 1

HCID 19689549N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamineYield 71%

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-chloro-4-pyridyl)-2-propen-1-one (1.72 g, 8.18 mmol), 3-ethoxycarbonyl-phenyl-guanidine nitrite (2.21 g, 8.18 mmol), sodium hydroxide (0.327 g, 8.18 mmol) in 2-butanol (40 mL) is heated to reflux for 24 hours before cooling to room temperature with the addition of water (40 mL). The solid is collected by filtration, washed with water and 2-propanol, and dried to give N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (2.06 g); ESI-MS (m/z): 355.1 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. filtrationThe solid is collected by filtration
  4. washwashed with water and 2-propanol
  5. customdried

Sources & evidence

ORD record
ord-da3d725cc9624e17bffa8e152a22dba3
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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