Potassium Carbonate → 3-Ethyl-5-[2-(6-methoxy-pyridin-3-ylamino)-pyrimidin-4-yl]-4-methyl-3H-thiazol-2-one

HRID 601445Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10](=[O:12])[N:9]([CH2:13][CH3:14])[C:8]=1[CH3:15])=O.[N+]([O-])(O)=O.[CH3:21][O:22][C:23]1[N: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>[CH2:13]([N:9]1[C:8]([CH3:15])=[C:7]([C:5]2[CH:4]=[CH:3][N:32]=[C:30]([NH:29][C:26]3[CH:27]=[N:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[N:31]=2)[S:11][C:10]1=[O:12])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

5-(3-Dimethylamino-acryloyl)-3-ethyl-4-methyl-3H-thiazol-2-one (80 mg, 0.333 mmol), N-(6-methoxy-pyridin-3-yl)-guanidine nitrate (76 mg, 0.333 mmol) and K2CO3 (185 mg, 1.332 mmol) were combined in of 2-methoxyethanol (4 mL) and the mixture was heated at 120° C. for 22 h. After cooling, the inorganics were filtered off and the filtrate was concentrated to dryness. The crude product was purified by SiO2 gel chromatography. Pooling of the desired fractions afforded the title compound (45 mg, 39%). 13C-NMR (d6-DMSO) δ: 14.5, 14.7, 37.3, 53.7, 109.0, 110.3, 128.4, 131.82, 132.4, 137.8, 138.4, 152.7, 159.5, 160.3, 164.7, 170.1. Remaining analytical data in Table 2.

Workup

temperatureAfter cooling
filtrationthe inorganics were filtered off
concentrationthe filtrate was concentrated to dryness
customThe crude product was purified by SiO2 gel chromatography

Sources & evidence

ORD record: ord-9f436ab52e6a4ffbad7dcc65bfad9eb2
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902361B2

Reaction notes

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