Triethylamine → 7-Methylthio-2-(2-methoxyphenyl)-4-oxo-3,4-dihydropyrimido[4,5-d]pyrimidine

HRID 372976Notes

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[C:13]1[C:18]([C:19](OCC)=[O:20])=[CH:17][N:16]=[C:15]([S:24][CH3:25])[N:14]=1.C(N(CC)CC)C>C(#N)C>[CH3:25][S:24][C:15]1[N:16]=[C:17]2[N:6]=[C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[O:2][CH3:1])[NH:7][C:19](=[O:20])[C:18]2=[CH:13][N:14]=1

Participants

Conditions

Temperature: 2 °C

Procedure

2-Methoxybenzamidine (from sodium, 0.15 g, in ethanol, 20 ml, and 2-methoxybenzamidine methanesulphonate, 1.70 g) was dissolved in acetonitrile (20 ml) and the resulting cooled (2° C.) solution was added to a cooled (2° C.) suspension of ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (2.33 g) in acetonitrile (20 ml). Triethylamine (0.66 g) was added and the reaction mixture was stirred at 2° C. for one hour and at ambient temperature for 18 hours. Acetonitrile was removed under reduced pressure and water (25 ml) was added. The mixture was cooled and a white solid was collected, washed with water and recrystallised from ethanol to yield the title compound, 0.46 g, m.p. 229°-231° C. (dec.).

Workup

additionwas added to
temperaturea cooled
customAcetonitrile was removed under reduced pressure and water (25 ml)
additionwas added
temperatureThe mixture was cooled
customa white solid was collected
washwashed with water
customrecrystallised from ethanol

Sources & evidence

ORD record: ord-b7f5b19725ec483b8291af3a9ae340bf
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162316

Reaction notes

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