Triethylamine → 6-benzyl-3-methyl-2-thioxo-2,3,5,6,7,8-hexahydropyrido[4,3-d]pyrimidin-4(1H)-one

HRID 742959Notes

Reaction equation

[NH2:1][C:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C:3]=1[C:15]([O:17]C)=O.[CH3:19][N:20]=[C:21]=[S:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:8]([N:5]1[CH2:6][CH2:7][C:2]2[NH:1][C:21](=[S:22])[N:20]([CH3:19])[C:15](=[O:17])[C:3]=2[CH2:4]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

788 g of methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate from a) were dissolved in 2.5 l of toluene, and 447 g of methyl isothiocyanate and 625 ml of triethylamine were added, with stirring. After stirring for 24 h at an internal temperature of 100° C., the mixture was allowed to cool to 20° C. and the precipitate was filtered off with suction and washed with toluene. After drying, this gave 420 g of crude 6 benzyl-3-methyl-2-thioxo-2,3,5,6,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-4-one, which was reacted further in c).

Workup

stirringAfter stirring for 24 h at an internal temperature of 100° C.
filtrationthe precipitate was filtered off with suction
washwashed with toluene
customAfter drying
customthis gave 420 g of crude 6 benzyl-3-methyl-2-thioxo-2,3,5,6,7,8-hexahydro-1H-pyrido[4,3-d]pyrimidin-4-one, which was reacted further in c)

Sources & evidence

ORD record: ord-1bcd1c5024054fa68378b4dd43afe805
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556854

Reaction notes

Loading…