3-(6-Chloropyrimidin-4-yl)benzoic acid → HCID 69486807, compound

HRID 498249Notes

Reaction equation

HRID 498249 reaction equation
CO[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([NH:16][CH3:17])[N:13]=[CH:12][N:11]=2)[CH:5]=1.ClC1N=CN=C(C2C=[C:28](C=CC=2)[C:29]([OH:31])=[O:30])C=1>CN>[C:4]([O:31][C:29](=[O:30])[CH2:28][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([NH:16][CH3:17])[N:13]=[CH:12][N:11]=2)[CH:5]=1)=[O:18])([CH3:9])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 223175383-(6-Chloropyrimidin-4-yl)benzoic acidHCID 69489895HCID 69489895, compound

Product 1

HCID 69486807HCID 69486807, compound

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Conditions

Temperature
50 °C

Procedure

The title compound was prepared from 3-[6-methylamino-pyrimidin-4-yl]-benzoic acid methyl ester [prepared by the following procedure: 3-(6-Chloro-pyrimidin-4-yl)-benzoic acid (1.49 g, 6 mmol) was heated in 40% aqueous methylamine (5 ml) to 80° C. for 14 h. The mixture was evaporated in vacuum and the residual oil was stirred in 1N HCl-MeOH (10 ml) for 36 h at 50° C. The crude product was purified by chromatography (silica gel, AcOEt) to give the methyl ester as yellow solid (0.62 g).] (0.60 g, 2.4 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a white solid (0.72 g).

Workup

  1. customprepared by the following procedure
  2. customThe mixture was evaporated in vacuum
  3. customThe crude product was purified by chromatography (silica gel, AcOEt)

Sources & evidence

ORD record
ord-960756a049f44a559eb838c23cf433bc
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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