3-(6-Chloropyrimidin-4-yl)benzoic acid → HCID 69486856, compound

HRID 498250Notes

Reaction equation

CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])[N:13]=[CH:12][N:11]=2)[CH:5]=1.ClC1N=CN=C(C2C=[C:31](C=CC=2)[C:32]([OH:34])=[O:33])C=1>COCCN>[C:4]([O:34][C:32](=[O:33])[CH2:31][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])[N:13]=[CH:12][N:11]=2)[CH:5]=1)=[O:21])([CH3:9])([CH3:5])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

The title compound was prepared from 3-[6-(2-methoxy-ethylamino)-pyrimidin-4-yl]-benzoic acid methyl ester [prepared by the following procedure: 3-(6-Chloro-pyrimidin-4-yl)-benzoic acid (1.0 g, 4.3 mmol) was heated in 2-methoxy-ethylamine (5 ml) to 80° C. for 1 h. The mixture was evaporated in vacuum and the residual oil was stirred in 1N HCl-MeOH (25 mL) for 18 h at 50° C. The crude product was purified by chromatography (silica gel, AcOEt-hexane 1:1) to give the methyl ester as light yellow solid (0.67 g).] (0.66 g, 2.3 mmol) by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a light yellow oil (0.93 g, not pure).

Workup

customprepared by the following procedure
customThe mixture was evaporated in vacuum
customThe crude product was purified by chromatography (silica gel, AcOEt-hexane 1:1)

Sources & evidence

ORD record: ord-c12ea2c5349f49d991bf7a2a6670ae5b
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949542B2

Reaction notes

Loading…