Potassium Carbonate → HCID 6539306, compound

HRID 855611Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:15])=[C:9]([C:13]#[N:14])[NH:10][C:11]=1[CH3:12])=O.[N+]([O-])(O)=O.[N+:21]([C:24]1[CH:25]=[C:26]([NH:30][C:31]([NH2:33])=[NH:32])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+]>COCCO>[CH3:15][C:8]1[C:7]([C:5]2[CH:4]=[CH:3][N:33]=[C:31]([NH:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=3)[N:32]=2)=[C:11]([CH3:12])[NH:10][C:9]=1[C:13]#[N:14]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 4-(3-dimethylamino-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carbonitrile (1.0 mmol, 0.22 g) and 3-nitrophenyl guanidine nitrate (1.5 mmol, 0.36 g) in 2-methoxyethanol (5 mL) was added K2CO3 (138 mg, 1.0 mmol). The reaction mixture was heated at 120° C. under N2 for 18 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (1:2 EtOAc/heptane) to afford the title compound as a light-yellow solid. M.p. 258–259° C. MS: [M+H]+=336.1 (C17H14N6O2 requires 334.3). 1H-NMR (CD3OD) δ: 2.39 (s, 3H, CH3), 2.49 (s, 3H, CH3), 6.94 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 7.50 (t, 1H, J=8.3 Hz, Ph-H), 7.81 (m, 1H, Ph-H), 7.94 (m, 1H, Ph-H), 8.45 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 8.94 (t, 1H, J=2.2 Hz, Ph-H).

Workup

customThe solvent was evaporated to dryness
customthe residue was purified by flash chromatography (1:2 EtOAc/heptane)

Sources & evidence

ORD record: ord-36795aa2281643d391b30dbee7e73a88
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262202B2

Reaction notes

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