Water → N-(2-Amino-6-(2-furyl)-5-nitropyrimidine-4-yl)-6-chloropyridine-3-carboxamide

HRID 732986Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10]([NH2:12])[N:9]=[C:8]([NH2:13])[C:7]=1[N+:14]([O-:16])=[O:15].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][N:19]=1.O>N1C=CC=CC=1>[NH2:12][C:10]1[N:9]=[C:8]([NH:13][C:22]([C:21]2[CH:20]=[N:19][C:18]([Cl:17])=[CH:26][CH:25]=2)=[O:23])[C:7]([N+:14]([O-:16])=[O:15])=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-(2-furyl)-5-nitropyrimidine-2,4-diamine (500 mg, 2.26 mmol) in pyridine (10 mL) was treated with 6-chloronicotinoyl chloride (438 mg, 2.49 mmol), stirred for 16 h at 80° C., cooled to room temperature, poured into water (100 mL) and extracted with EtOAc (2×25 mL) and the combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (3:2)] to give the title compound (430 mg, 82%) as a yellow solid; NMR δH (400 MHz, DMSO) 11.14 (1H, s), 8.86 (1H, d, J 2.5 Hz), 8.27 (1H, dd, J 8.5, 2.5 Hz), 7.93 (1H, m), 7.77 (2H, br s), 7.65 (1H, d, J 7.5 Hz), 7.09 (1H, d, J 4.5 Hz), 6.72-6.70 (1H, m); Retention time 2.41 min.

Workup

temperaturecooled to room temperature
extractionextracted with EtOAc (2×25 mL)
dry with materialthe combined organic phase was dried (MgSO4)
concentrationconcentrated in vacuo
custompurified by chromatography [SiO2; isohexane:EtOAc (3:2)]

Sources & evidence

ORD record: ord-a4e7f346bdb4488091fa94929fdf6546
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589097B2

Reaction notes

Loading…