4-Aminopyridine → [2-(2-Fluoro-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-pyridin-4-yl-amine

HRID 1010825Notes

Reaction equation

HRID 1010825 reaction equation
Cl[C:2]1[C:3]2[CH:17]=[CH:16][S:15][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:7]=1.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>C(O)(C)C.Cl.O1CCOCC1>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:3]2[CH:17]=[CH:16][S:15][C:4]=2[N:5]=1

Participants

5

Reactant 2

HCID 17274-AminopyridineHCID 211043364-Chloro-2-(2-fluorophenyl)thieno[2,3-d]pyrimidine

Product 1

HCID 21104304[2-(2-Fluoro-phenyl)-thieno[2,3-d]pyrimidin-4-yl]-pyridin-4-yl-amineYield 87.8%

Reagents, catalysts & solvents 2

HCID 204431481,4-Dioxane hydrochlorideCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-2-(2-fluoro-phenyl)-thieno[2,3-d]pyrimidine (110 mg, 0.41 mmole) and 4-aminopyridine (78 mg, 0.830 mmole) were combined in isopropanol (3 ml), then 4 drops of 4 M HCl/dioxane were added and the reaction mixture was heated to 80° C. for 7 hours. The reaction mixture was cooled and the product was isolated by filtration, washed with minimum cold methanol and dried under vacuum to give 116 mg of product (yield: 86%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe product was isolated by filtration
  3. washwashed with minimum cold methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2c4e4a594a054f47b3dd846b08bc0bde
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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