4-Fluoroaniline → {2-[(4-Fluorophenyl)amino]-6-methylpyrimidin-4-yl}methanol

HRID 242148Notes

Reaction equation

HRID 242148 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C(OCC)C>[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([CH3:10])[N:3]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 59462115(2-Chloro-6-methylpyrimidin-4-yl)methanol

Product 1

HCID 59278633{2-[(4-Fluorophenyl)amino]-6-methylpyrimidin-4-yl}methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

50 mg (0.32 mmol) of the compound from example 5A and 350 mg (3.15 mmol) of 4-fluoroaniline are stirred together at 160° C. for 2 h. The reaction mixture is then poured into 10 ml of diethyl ether. The precipitate is filtered off and discarded and the filtrate is then purified chromatographically on silica gel 60 (mobile phase: gradient dichloromethane→dichloromethane/ethanol 50:1).

Workup

  1. filtrationThe precipitate is filtered off
  2. customthe filtrate is then purified chromatographically on silica gel 60 (mobile phase: gradient dichloromethane→dichloromethane/ethanol 50:1)

Sources & evidence

ORD record
ord-23d0182987f647d7afe91c7ff6225499
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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