Malononitrile → 8-Ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 1893913Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][C:10]1[C:15]([CH:16]=O)=[C:14]([CH3:18])[N:13]=[C:12]([S:19][CH3:20])[N:11]=1)[CH3:8].[C:21](#[N:25])[CH2:22][C:23]#[N:24]>C(O)C>[CH2:7]([N:9]1[C:10]2[N:11]=[C:12]([S:19][CH3:20])[N:13]=[C:14]([CH3:18])[C:15]=2[CH:16]=[C:22]([C:23]#[N:24])[C:21]1=[NH:25])[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (0.539 g, 3.90 mmol) was added to a suspension of 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carbaldehyde (0.413 g, 1.95 mmol) from above, and malononitrile (0.194 g, 2.93 mmol) in absolute ethanol (15.0 mL) and heated to 70° C. After one h, the reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL) and washed with saturated NaHCO3 (50 mL), and brine. The organic phase was separated and concentrated in vacuo. The residue was precipitated with ethyl acetate and hexanes to give 8-ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile as a brown solid that was used in the subsequent step without further purification.

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with ethyl acetate (50 mL)
washwashed with saturated NaHCO3 (50 mL), and brine
customThe organic phase was separated
concentrationconcentrated in vacuo
customThe residue was precipitated with ethyl acetate and hexanes

Sources & evidence

ORD record: ord-cf54140ea40c4cd69277dbbd08ef281c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513266B2

Reaction notes

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