Diisopropylethylamine → 2-(2-(6-(2,4-dimethoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl)guanidine

HRID 77542

Reaction equation

C(N(C(C)C)CC)(C)C.Cl.[NH2:11][CH2:12][CH2:13][N:14]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])=[CH:18][C:17](=[O:30])[NH:16][C:15]1=[S:31].Cl.[N:33]1([C:38](N)=[NH:39])C=CC=N1>CN(C=O)C.CCO>[CH3:29][O:28][C:21]1[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:20]=1[C:19]1[N:14]([CH2:13][CH2:12][N:11]=[C:38]([NH2:39])[NH2:33])[C:15](=[S:31])[NH:16][C:17](=[O:30])[CH:18]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Diisopropylethylamine (0.22 mL, 1.3 mmol) was added to a suspension of 1-(2-aminoethyl)-6-(2,4-dimethoxyphenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one hydrochloride (181.6 mg, 0.528 mmol) (the product of Example 6) and 1H-pyrazole-1-carboxamidine hydrochloride (90.6 mg, 0.618 mmol) in DMF (0.55 mL). After heating for 1 h at 55° C., the reaction mixture was cooled to ambient temperature, diluted with EtOH (1.6 mL), and the solid product collected by vacuum filtration, rinsing with additional EtOH. The isolated solid was re-suspended in EtOH (2.1 mL) for 3 h at r.t. before being collected again by vacuum filtration and rinsing with additional EtOH. The desired product was obtained, after drying, as a colorless solid. Solubility data for this product is consistent with it being in its zwitterionic form.

Workup

temperaturethe reaction mixture was cooled to ambient temperature
filtrationthe solid product collected by vacuum filtration
washrinsing with additional EtOH
filtrationbefore being collected again by vacuum filtration
washrinsing with additional EtOH

Sources & evidence

ORD record: ord-c431bce398914ea1877c0b876440c5ad
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841314B2

Linked notes

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