Water → 2-Anilino-4-(1-cyclobutyl-2-methylimidazol-5-yl)pyrimidine

HRID 1723661Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:10]([CH3:16])=[N:9][CH:8]=1)=O.C(=O)(O)O.[C:22]1([NH:28][C:29]([NH2:31])=[NH:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[O-].[Na+].O>CC(N(C)C)=O>[NH:28]([C:29]1[N:31]=[C:5]([C:7]2[N:11]([CH:12]3[CH2:13][CH2:14][CH2:15]3)[C:10]([CH3:16])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 160 °C

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-cyclobutyl-2-methylimidazole (Method 37; 466 mg, 2 mmol), phenylguanidine hydrogen carbonate (434 g, 2.2 mmol) and sodium methoxide (238 mg, 4.4 mmol) were suspended in anhydrous DMA (5 ml) and the mixture heated at 160° C. for 3 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 was triturated with ether, collected by filtration and air dried to give the title compound (205 mg, 35%) as a brown solid. NMR: 1.63 (m, 2H), 2.35 (m, 4H), 2.53 (s, 3H), 5.5 (m, 1H), 6.96 (d, 2H), 7.28 (m, 4H), 7.70 (d, 2H), 8.39 (d, 1H), 9/45 (s, 1H); m/z 306.

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 was triturated with ether
filtrationcollected by filtration and air
customdried

Sources & evidence

ORD record: ord-60c7763639cb432c8278fad5165a8f4d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485638B2

Reaction notes

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