2-Chloropyrimidine → (3-Imidazo[1,2-a]pyridine-3-yl-phenyl)-pyrimidin-2-yl amine

HRID 1093523Notes

Reaction equation

[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CC([O-])(C)C.[Na+]>O1CCOCC1>[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH:16][C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture 3-imidazo[1,2-a]pyridin-3-yl-phenylamine (210 mg, 1.0 mmol), 2-chloropyrimidine (115 mg, 1 mmol) and NaOtBu (100 mg, 1.0 mmol) in dry dioxane (2 ml) was stirred and heated at 100° C. under N2 for 18 hours. After cooling to RT the mixture was partitioned between EtOAc/H2O. The layers were separated and the aqueous layer was extracted with EtOAc (×2). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by preparative HPLC to give the title compound (20 mg, solid). MS: [M+H]+ 288

Workup

temperatureAfter cooling to RT the mixture
customwas partitioned between EtOAc/H2O
customThe layers were separated
extractionthe aqueous layer was extracted with EtOAc (×2)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-59f670709a45495ab3d4c24489d471bf
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08131527B1

Reaction notes

Loading…