Water → 2-Anilino-4-(1-ethyl-2,4dimethylimidazol-5-yl)pyrimidine

HRID 268587Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH2:12][CH3:13])[C:10]([CH3:14])=[N:9][C:8]=1[CH3:15])=O.C(=O)(O)O.[C:21]1([NH:27][C:28]([NH2:30])=[NH:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[O-].[Na+].O>CC(N(C)C)=O>[NH:27]([C:28]1[N:30]=[C:5]([C:7]2[N:11]([CH2:12][CH3:13])[C:10]([CH3:14])=[N:9][C:8]=2[CH3:15])[CH:4]=[CH:3][N:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 150 °C

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-ethyl-2,4-dimethylimidazole (Method 10; 5.65 g, 25.6 mmol), phenylguanidine hydrogen carbonate (6.05, 30.7 mmol) and sodium methoxide (3.47 g, 64.2 mmol) were suspended in anhydrous DMA (80 ml) and the mixture heated at 150° C. for 18 hours. The reaction mixture was allowed to cool to ambient temperature and poured into water (50 ml). The solution was extracted EtOAc (2×50 ml). The combined extracts were washed with water (2×50 ml) and then brine (2×50 ml), dried and the volatiles removed by evaporation. The residue purified by flash silica chromatography DCM:MeOH (increasing in polarity from 100:0 to 96:4) to give the title compound (5.2 g, 70%) as an orange oil. NMR: 1.06 (t, 3H), 2.22 (s, 3H), 2.34 (s, 3H), 4.32 (q, 2H), 6.83 (d, 1H), 6.97 (t, 1H), 7.28 (t, 2H), 7.70 (d, 2H), 8.43 (d, 2H), 9.40 (s, 1H); m/z 294.

Workup

temperatureto cool to ambient temperature
extractionThe solution was extracted EtOAc (2×50 ml)
washThe combined extracts were washed with water (2×50 ml)
dry with materialbrine (2×50 ml), dried
customthe volatiles removed by evaporation
customThe residue purified by flash silica chromatography DCM

Sources & evidence

ORD record: ord-138f7888e1f146aba0d8f346c4a2dd0b
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446105B2

Reaction notes

Loading…