Hydrochloric Acid → 6-(4-fluorophenyl)-2-phenylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1396791Notes

Reaction equation

HRID 1396791 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=O.[C:19](#[N:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>O1CCOCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[S:3][C:2]3[N:1]=[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:26][C:7](=[O:9])[C:6]=3[CH:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7505BenzonitrileHCID 21529229Ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate

Product 1

HCID 667587136-(4-fluorophenyl)-2-phenylthieno[2,3-d]pyrimidin-4(3H)-oneYield 82.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.2 g, 0.75 mmol) and benzonitrile (0.23 g, 2.26 mmol) in dioxane (4 ml) was added 4M HCl in dioxane (4 ml). The mixture was stirred at room temperature overnight. The precipitate was filtered off, washed with diethyl ether and dried. The solid was redissolved in DMF and the mixture was heated at 100° C. for 3 hours. The solvents were removed under reduced pressure. The residue was diluted with water and the solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1) to yield the title compound as a white solid (0.20 g, 82%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with diethyl ether
  3. customdried
  4. dissolutionThe solid was redissolved in DMF
  5. temperaturethe mixture was heated at 100° C. for 3 hours
  6. customThe solvents were removed under reduced pressure
  7. additionThe residue was diluted with water
  8. filtrationthe solid was filtered off
  9. washwashed with water
  10. customdried
  11. customThe crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1)

Sources & evidence

ORD record
ord-f421829f76094de89de48fd8428f88d0
Source dataset
uspto-grants-2014_12
Patent number
US08901132B2

Reaction notes

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