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

HRID 718323Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[S:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[F:27])[NH2:23]>ClCCCl.CC(O)(C)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:3]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[S:9][C:4]=3[N:5]=[C:6]([CH3:8])[N:7]=2)[CH:24]=[CH:25][C:26]=1[F:27]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidine (15 mg, 0.05 mmol) in 1,2-dichloroethane/t-BuOH (1:1, 2 ml) was added 3-chloro-4-fluoroaniline (16 mg, 0.11 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 (11 mg, 53%).

Workup

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

Sources & evidence

ORD record: ord-755a3400418840ecb281058be610e93c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193741B2

Reaction notes

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