Hydrochloric Acid → 3-Methylthio-8-oxo-6-(2-methoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 1936694Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[NH:6].Cl.[CH3:13][S:14][C:15]1[N:16]=[N:17][C:18]([C:22](OCC)=[O:23])=[C:19](Cl)[N:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:13][S:14][C:15]1[N:16]=[N:17][C:18]2[C:22](=[O:23])[NH:7][C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[O:2][CH3:1])=[N:6][C:19]=2[N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A cooled (0° C.) solution of 2-methoxybenzamidine (from 1.97 g of the hydrochloride) in acetonitrile (17 ml) was added to a cooled solution of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared from 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.08 g, and thionyl chloride, 20 ml) in acetonitrile (17 ml). Triethylamine (0.51 g) was added and the reaction mixture was stirred with cooling (0° C.) for one hour and then at ambient temperature for 17 hours to afford a yellow solid which was washed with acetonitrile and ether to afford the crude title compound (1.39 g). A sample (0.35 g) of this was washed twice with boiling methanol to afford the title compound, 0.25 g, m.p. 267.5-268.5° C. The remaining material (1.04 g) was similarly treated with boiling methanol to afford the title compound, 0.91 g, m.p. 266-268° C.

Workup

customat ambient temperature for 17 hours to afford a yellow solid which
washwas washed with acetonitrile and ether
customto afford the crude title compound (1.39 g)
washA sample (0.35 g) of this was washed twice with boiling methanol

Sources & evidence

ORD record: ord-1e21b102d6ba4355b92753b4da42a426
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391885B1

Reaction notes

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