Hydrochloric Acid → 2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]benzoic acid

HRID 1508713Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([CH3:10])[N:5]=[C:4]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[N:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([Br:27])=[C:22]([CH:26]=1)[C:23]([OH:25])=[O:24].Cl>O1CCOCC1.CC(O)=O>[Br:27][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:2]2[C:7]([CH2:8][CH3:9])=[C:6]([CH3:10])[N:5]=[C:4]([C:11]3[S:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[N:3]=2)=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]

Participants

Conditions

Temperature: 110 °C

Procedure

A 18-mL vial was charged with 4-chloro-2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidine (87 mg, 0.318 mmol, 1.05 eq.), 5-amino-2-bromo-benzoic acid (65 mg, 0.3 mmol, 1 eq.). AcOH (1 ml) and 4 N HCl in dioxane (5 drops). The resulting mixture was stirred under Ar at 110° C. for 2 hr. After cooling to rt, The volatile material was removed under reduced pressure and the residue was treated with dichloromethane to give the title compound (105 mg, 77% yield).

Workup

temperatureAfter cooling to rt
customThe volatile material was removed under reduced pressure
additionthe residue was treated with dichloromethane

Sources & evidence

ORD record: ord-006838468bfb440b9b4c7e2db8866fd6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221843B2

Reaction notes

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