3-Fluoroaniline → HCID 22386545, compound

HRID 1072420Notes

Reaction equation

HRID 1072420 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CC(C)([O-])C.[K+].C(S[C:18]1[N:23]2[CH:24]=[CH:25][N:26]=[C:22]2[CH:21]=[C:20]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)[N:19]=1)C>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:18]2[N:23]3[CH:24]=[CH:25][N:26]=[C:22]3[CH:21]=[C:20]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=3)[N:19]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 11301507HCID 11301507, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22386545HCID 22386545, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of m-fluoroaniline (88.90 mg, 0.8 mmol) in 1.5 ml of dry DMSO was added, potassium tert-butoxide (94.26 mg, 0.84 mmol), and 5-ethylsulfenyl-7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin (126.16 mg, 0.4 mmol). The resulting solution was stirred overnight and 3 ml of ice water was added. The produced precipitate was collected by filtration, and washed with water, 2-propanol, and ether to give crude product of (3-fluorophenyl)-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-yl]amine. The crude product was purified by preparative TLC to give the pure product (127.000 mg, 87.1%).

Workup

  1. filtrationThe produced precipitate was collected by filtration
  2. washwashed with water, 2-propanol, and ether

Sources & evidence

ORD record
ord-9c914b67e6a4425d9ad570d32f8b625a
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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