Potassium Carbonate → 2-anilino-4-(1H-pyrrol-3-yl) pyrimidine deriv. 8i

HRID 855612Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:16])=[C:9]([C:13]([NH2:15])=[O:14])[NH:10][C:11]=1[CH3:12])=O.[N+]([O-])(O)=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>COCCO>[F:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]2[N:32]=[C:5]([C:7]3[C:8]([CH3:16])=[C:9]([C:13]([NH2:15])=[O:14])[NH:10][C:11]=3[CH3:12])[CH:4]=[CH:3][N:31]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-(3-Dimethylamino-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid amide (100 mg, 0.43 mmol), 4-fluorophenylguanidine nitrate (139 mg, 0.65 mmol) and K2CO3 (94 mg, 0.68 mmol) were partially dissolved in 2-methoxyethanol (5 mL) and heated at 120° C. for 18 h. The mixture was concentrated in vacuo and purified by SiO2 chromatography (EtOAc/MeOH gradient elution). The crude product was triturated in iPr2O to afford the title compound (31 mg) as a buff solid. M.p. 93.5–96.8° C. MS: [M+H+]=326.9 (C17H16FN5O requires 325.3). 1H-NMR (DMSO-d6) δ: 2.36 (s, 3H, CH3), 2.39 (s, 3H, CH3), 6.79 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 6.92 (br. s, 2H, NH), 7.07 (t, 2H, J=8.5 Hz, Ph-H), 7.76–7.78 (m, 2H, Ph-H), 8.36 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.41 (s, 1H, NH), 11.24 (br. s, 1H, NH).

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by SiO2 chromatography (EtOAc/MeOH gradient elution)
customThe crude product was triturated in iPr2O

Sources & evidence

ORD record: ord-743930c1d0a8496098131c14b6707aad
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262202B2

Reaction notes

Loading…