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3-Chloro-4-fluoroaniline → N-(3-chloro-4-fluorophenyl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 718311
Notes
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Reaction equation

HRID 718311 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[F:26])[NH2:22]>ClCCCl.CC(O)(C)C>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:2]2[C:3]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=4)[S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:23]=[CH:24][C:25]=1[F:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 866624414-Chloro-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine

Product 1

HCID 56941891N-(3-chloro-4-fluorophenyl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amineYield 50%

Reagents, catalysts & solvents 1

HCID 21868497Tert-butyl alcohol 1,2-dichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine (40 mg, 0.15 mmol) in 1,2-dichloroethane/t-BuOH (1:1, 1 ml) was added 3-chloro-4-fluoroaniline (22 mg, 0.15 mmol). The mixture was heated at 90° C. for 2 days. After cooling down to room temperature, the solvents were removed under reduced pressure. The crude residue was purified by silica gel chromatography (CH2Cl2/MeOH 100:1) to yield the title compound as a white solid (28 mg, 50%).

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe solvents were removed under reduced pressure
  3. customThe crude residue was purified by silica gel chromatography (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-e53833e1c9b14a0c9744490493b716dd
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193741B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes