Hydrochloric Acid → N-[2-Amino-6-(4-pyridinyl)-4-pyrimidinyl]-N-[4-(1-benzofuran-4-yloxy)-3-fluoro-phenyl]amine

HRID 16441Notes

Reaction equation

HRID 16441 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=3[F:18])[C:4]=2[CH:3]=[CH:2]1.Cl[C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=[C:22]([NH2:32])[N:21]=1.Cl.[OH-].[Na+]>O>[NH2:32][C:22]1[N:21]=[C:20]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][C:9]3[C:4]4[CH:3]=[CH:2][O:1][C:5]=4[CH:6]=[CH:7][CH:8]=3)=[C:12]([F:18])[CH:13]=2)[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[N:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 179793044-(1-Benzofuran-4-yloxy)-3-fluorophenylamineHCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 17979305N-[2-Amino-6-(4-pyridinyl)-4-pyrimidinyl]-N-[4-(1-benzofuran-4-yloxy)-3-fluoro-phenyl]amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

32 mg (0.13 mmol) of 4-(1-benzofuran-4-yloxy)-3-fluorophenylamine (from example XXIII) and 28.5 mg (0.14 mmol) of 4-chloro-6-(4-pyridinyl)-2-pyrimidine-amine (from example XXIX) are suspended in 1.5 ml of water, and 19 μl of concentrated hydrochloric acid are added. The reaction mixture is heated at reflux overnight, resulting in the formation of a brown precipitate. Using 1N sodium hydroxide solution, the suspension is adjusted to pH 10. The precipitate is filtered off with suction and the filtrate is discarded. The crude product is purified by preparative HPLC.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customresulting in the formation of a brown precipitate
  4. filtrationThe precipitate is filtered off with suction
  5. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-47a28c6f829248468da0cbc0fbf81b05
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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