4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → 7-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

HRID 372974Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[NH:8])[CH2:2][CH3:3].Cl[C:15]1[C:20]([C:21](OCC)=[O:22])=[CH:19][N:18]=[C:17]([S:26][CH3:27])[N:16]=1>CC(O)C>[CH3:27][S:26][C:17]1[N:18]=[C:19]2[N:8]=[C:7]([C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[O:4][CH2:1][CH2:2][CH3:3])[NH:9][C:21](=[O:22])[C:20]2=[CH:15][N:16]=1

Participants

Conditions

Temperature: 2 °C

Procedure

2-Propoxybenzamidine (from sodium, 0.3 g, in ethanol, 50 ml, and 2-propoxybenzamidine hydrochloride, 2.77 g) was dissolved in 2-propanol (20 ml) and the resulting cooled (2° C.) solution was added to a cooled (2° C.) solution of ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (2 g) in 2-propanol (30 ml). The reaction mixture was stirred at 2° C. for 2 hours and was then left overnight at ambient temperature to yield a white crude product, 1.18 g, m.p. 179°-181° C. Recrystallisation from ethanol yielded the title compound, 0.92 g, m.p. 186°-187° C.

Workup

additionwas added to
waitwas then left overnight at ambient temperature
customto yield a white crude product, 1.18 g, m.p. 179°-181° C
customRecrystallisation from ethanol

Sources & evidence

ORD record: ord-fdddee2bad9e4048806b9e9b48afac0d
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162316

Reaction notes

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